Substituted Triazines for Malaria Treatment and Chemoprophylaxis

ABSTRACT

Disclosed herein are triazine compounds and methods of making and using thereof to treat malaria, provide chemoprophylaxis, and/or treat or inhibit infection by one or more  Plasmodium  spp.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Application No. 61/779,331, filed 13 Mar. 2013, which is herein incorporated by reference in its entirety.

ACKNOWLEDGEMENT OF GOVERNMENT SUPPORT

This invention was made by employees of the U.S. Army Medical Research & Materiel Command. The Government has certain rights in the invention.

NO BIOLOGICAL SEQUENCES

This application refers to chemical names and formulas and does not refer to any biological sequences that require a Sequence Listing.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to novel triazine compounds and compositions and methods of using to treat malaria and/or chemoprophylaxis.

2. Description of the Related Art

Malaria is the number one infectious disease threat for deployed US troops. There is a critical need for the discovery of new classes of anti-malaria drugs due to the therapeutic challenges emanating from the emergence of resistance in many structural classes of current therapies.

SUMMARY OF THE INVENTION

The present invention is directed to novel triazine compounds, compositions, and methods making and using to treat malaria, provide chemoprophylaxis, and/or treat or inhibit infections by one or more Plasmodium spp. in subjects.

Both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the invention as claimed. The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute part of this specification, illustrate several embodiments of the invention, and together with the description serve to explain the principles of the invention.

DETAILED DESCRIPTION OF THE INVENTION Definitions

For purposes of the present invention, as described and claimed herein, the following terms and phrases are defined as follows:

The term “patient” and “subject” are synonyms and mean all mammals, including humans and animals such as cows, dogs, cats, goats, sheep, pigs, rodents, and rabbits.

A “therapeutically effective amount”, unless otherwise indicated, refers to an amount of one or more compounds of the present invention that, when administered to a subject, (i) treats or inhibits the particular disease, condition, or disorder, (ii) attenuates, ameliorates, or eliminates one or more symptoms of the particular disease, condition, or disorder, and/or (iii) inhibits or delays the onset of one or more symptoms of the particular disease, condition, or disorder.

“Treatment”, “treating”, and the like, unless otherwise indicated, refers to reversing, alleviating, or inhibiting the progress of the particular disease, condition, or disorder to which such term applies, or one or more symptoms of the particular disease, condition, or disorder. These terms also encompass, depending on the condition of the mammal, preventing or inhibiting the onset of the particular disease, condition, or disorder or symptoms thereof. Treatment can refer to prophylactic treatment, i.e., administration of one or more compounds of the present invention to a subject that is not at the time of administration afflicted with the particular disease, condition, or disorder.

As provided herein, a bond is represented by a line, such as “-”, or the symbol “

”. The line and symbol represent that the bond is the point of attachment between two molecular subunits.

An “alkyl” refers to a straight or branched chain monovalent radical of saturated and/or unsaturated carbon atoms and hydrogen atoms, such as methyl (Me) ethyl (Et) propyl (Pr) isopropyl (i-Pr) butyl (n-Bu) isobutyl (i-Bu) t-butyl (t-Bu) (sec-Bu) ethenyl, pentenyl, butenyl, propenyl, ethynyl, butynyl, propynyl, pentynyl, hexynyl, and the like, which may be unsubstituted (i.e., contain only carbon and hydrogen) or substituted by one or more substituents as defined below (e.g., one or more halogen, such as F, Cl, Br, or I, with F and Cl being preferred). The term “(C₁-C₆)alkyl” as used herein refers to a straight or branched hydrocarbon from 1 to 6 carbon atoms and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, and the like. The (C₁-C₆)alkyl group optionally can be substituted with one or more substituents as defined below. The term “(C₁-C₃)alkyl” as used herein refers to a straight or branched hydrocarbon of from 1 to 3 carbon atoms and includes methyl, ethyl, n-propyl, isopropyl, and the like. The (C₁-C₃)alkyl group optionally can be substituted with one or more of more substituents as defined below.

The term “halo” includes chlorine, fluorine, bromine, and iodine.

The term “haloalkyl” refers to a branched or straight chained alkyl group in which at least one hydrogen atom is replaced with a halogen, e.g., (C₁-C₆)haloalkyl=a branched or straight chained alkyl group containing from 1 to 6 carbon atoms, in which at least one hydrogen atom is replaced with a halogen. Examples of haloalkyls include chloromethyl, trichloromethyl, fluoromethyl, trifluoromethyl, and the like.

A “hydroxyl” refers to the radical —OH.

The term “alkoxy” refers to the radical —OR, where R is a straight or branched chain alkyl group. Exemplary alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, and the like. A “(C₁-C₆)alkoxy” refers to a straight or branched chain alkoxy group containing from 1 to 6 carbon atoms and a “(C₁-C₃)alkoxy” refers to a straight or branched chain alkoxy group containing from 1 to 3 carbon atoms.

An “alkoxycarbonyl” refers to the radical —C(O)OR, where R is an alkyl group.

The term “haloalkoxy” refers to a branched or straight chained alkoxy group in which at least one hydrogen atom is replaced with a halogen, e.g., (C₁-C₆)haloalkoxy=a branched or straight chained alkoxy group containing from 1 to 6 carbon atoms, in which at least one hydrogen atom is replaced with a halogen. Examples of haloalkoxys include chloromethoxy, trichloromethoxy, fluoromethoxy, trifluoromethoxy, and the like.

A “cycloalkyl” refers to a non-aromatic monovalent monocyclic, bicyclic, or tricyclic radical comprising 3-14 carbon ring atoms, each of which may be saturated or unsaturated, and which may be unsubstituted or substituted by one or more suitable substituents as defined below, and to which may be fused one or more heterocycloalkyl groups, aryl groups, or heteroaryl groups, which themselves may be unsubstituted or substituted by one or more substituents. The term “(C₃-C₈)cycloalkyl” means a hydrocarbon ring containing from 3 to 8 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Where possible, the cycloalkyl group may contain double bonds, for example, 3-cyclohexen-1-yl. The cycloalkyl ring may be unsubstituted or optionally may be substituted by one or more substituents selected from (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)thioalkoxy, hydroxy, thiol, halo, formyl, carboxyl, amino, aminoalkyl, —CO₂(C₁-C₆)alkyl, —CO(C₁-C₆)alkyl, —C(O)N(C₁-C₆)alkyl, aryl, and heteroaryl.

The term “aryl” means a cyclic or polycyclic aromatic ring having from 5 to 12 carbon atoms, and may be unsubstituted or substituted by one or more suitable substituents as defined below, and to which may be fused one or more cycloalkyl groups, heterocycloalkyl groups, or heteroaryl groups, which themselves may be unsubstituted or substituted by one or more suitable substituents.

A “heteroaryl” refers to an aromatic monovalent monocyclic, bicyclic, or tricyclic radical comprising 4-18 ring members, including 1-5 heteroatoms selected from nitrogen, oxygen, and sulfur, which may be unsubstituted or substituted by one or more suitable substituents as defined below, and to which may be fused one or more cycloalkyl groups, heterocycloalkyl groups, or aryl groups, which themselves may be unsubstituted or substituted by one or more suitable substituents.

A “heterocycloalkyl” refers to a non-aromatic monovalent monocyclic, bicyclic, or tricyclic radical, which is saturated or unsaturated, comprising 3-18 ring members, which includes 1-5 heteroatoms selected from nitrogen, oxygen, and sulfur, where the radical is unsubstituted or substituted by one or more suitable substituents as defined below, and to which may be fused one or more cycloalkyl groups, aryl groups, or heteroaryl groups, which themselves may be unsubstituted or substituted by one or more suitable substituents.

A “heterocycle” refers to a heteroaryl or heterocycloalkyl as defined above.

An “acyl” refers to a —C(O)—R radical, where R is a suitable substituent as defined below.

A “thioacyl” refers to a —C(S)—R radical, where R is a suitable substituent as defined below.

A “sulfonyl” refers to a —SO₂R radical, where R is a suitable substituent as defined below.

The term “amino” refers to —NH₂.

The term “alkylamino” refers to an amino moiety substituted with one (i.e., —NHR) or two (i.e., —NRR′) (C₁-C₆)alkyl groups which may be the same or different. Examples of such alkylamino groups include aminomethyl, dimethylamino, aminomethylethyl, aminomethylpropyl, and the like.

The term “amino group” refers to amino and alkylamino groups.

An “alkylsulfonyl” refers to the radical —SO₂R, where R is an alkyl group.

An “alkylaminocarbonyl” refers to the radical —C(O)NHR, where R is an alkyl group.

A “dialkylaminocarbonyl” refers to the radical —C(O)NRR′, where each R may be the same or different alkyl group.

A “mercapto” refers to the radical —SH.

An “alkylthio” refers to the radical —SR, where R is an alkyl group.

A “carboxyl” refers to the radical —C(O)OH.

A “carbamoyl group” refers to the radical C(O)NH₂.

An “aryloxyl” refers to the radical —O

A “heteroaryloxyl” refers to the radical —O-HAR, where HAR is a heteroaryl group.

An “arylthio” refers to the radical —S-ARY, where ARY is an aryl group.

A “heteroarylthio” refers to the radical —S-HAR, where HAR is a heteroaryl group.

A “leaving group” (Lv) refers to any suitable group that will be displaced by a substitution reaction. One of ordinary skill in the art will know that any conjugate base of a strong acid can act as a leaving group. Illustrative examples of suitable leaving groups include, but are not limited to, —F, —Cl, —Br, alkyl chlorides, alkyl bromides, alkyl iodides, alkyl sulfonates, alkyl benzenesulfonates, alkyl p-toluenesulfonates, alkyl methanesulfonates, triflate, and any groups having a bisulfate, methyl sulfate, or sulfonate ion.

A “protecting group” is intended to refer to groups that protect one or more inherent functional group from premature reaction. Suitable protecting groups may be routinely selected by those skilled in the art in light of the functionality and particular chemistry used to construct the compound. Examples of suitable protecting groups are described, for example, in Greene and Wuts, Protective Groups in Organic Synthesis, 3^(rd) edition, John Wiley and Sons, New York, N.Y. (1999).

The term “suitable organic moiety” refers to any organic moiety recognizable, such as by routine testing, to those skilled in the art as not adversely affecting the inhibitory activity of the inventive compounds. Illustrative examples of suitable organic moieties include, but are not limited to, hydroxyl groups, alkyl groups, oxo groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, acyl groups, sulfonyl groups, mercapto groups, alkylthio groups, alkoxyl groups, carboxyl groups, amino groups, alkylamino groups, dialkylamino groups, carbamoyl groups, arylthio groups, heteroarylthio groups, and the like.

In general, the various moieties or functional groups for variables in the formulae may be “optionally substituted” by one or more suitable “substituents”. The term “substituent” or “suitable substituent” refers to any suitable substituent that may be recognized or selected, such as through routine testing, by those skilled in the art. Illustrative examples of useful substituents are those found in the exemplary compounds that follow, as well as halogen (chloro, iodo, bromo, or fluoro) (C₁-C₆)alkyl; (C₁-C₆)alkenyl; (C₁-C₆)alkynyl; hydroxyl; (C₁-C₆)alkoxyl; amino; nitro; thiol; thioether; imine; cyano; amido; phosphonato; phosphine; carboxyl; carbonyl; aminocarbonyl; thiocarbonyl; sulfonyl; sulfonamine; sulfonamide; ketone; aldehyde; ester; oxygen (═O) haloalkyl (e.g., trifluoromethyl) carbocyclic cycloalkyl, which may be monocyclic or fused or non-fused polycyclic (e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl) or a heterocycloalkyl, which may be monocyclic or fused or non-fused polycyclic (e.g., pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, or thiazinyl) carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic aryl (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothiophenyl, or benzofuranyl) amino (primary, secondary, or tertiary) nitro; thiol; thioether, O—(C₁-C₆)alkyl; O-aryl, aryl; aryl-(C₁-C₆)alkyl; CO₂CH₃; CONH₂; OCH₂CONH₂; NH₂; SO₂NH₂; OCHF₂; CF₃; OCF₃; and the like. Such moieties may also be optionally substituted by a fused-ring structure or bridge, for example OCH₂—O. All of these substituents may optionally be further substituted with a substituent selected from groups such as hydroxyl groups, halogens, oxo groups, alkyl groups, acyl groups, sulfonyl groups, mercapto groups, alkylthio groups, alkyloxyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, carboxyl groups, amino groups, alkylamino groups, dialkylamino groups, carbamoyl groups, aryloxyl groups, heteroaryloxyl groups, arylthio groups, heteroarylthio groups, and the like.

The term “optionally substituted” is intended to expressly indicate that the specified group is unsubstituted or substituted by one or more suitable substituents, unless the optional substituents are expressly specified, in which case the term indicates that the group is unsubstituted or substituted with the specified substituents. As defined above, various groups may be unsubstituted or substituted (i.e., they are optionally substituted) unless indicated otherwise herein (e.g., by indicating that the specified group is unsubstituted).

A “solvate” refers to a pharmaceutically acceptable solvate form of a specified compound that retains the biological effectiveness of such compound. Examples of solvates include compounds of the invention in combination with water, isopropanol, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, ethanolamine, or acetone. Those skilled in the art of organic chemistry will appreciate that many organic compounds can form complexes with solvents in which they are reacted or from which they are precipitated or crystallized. These complexes are known as “solvates”. For example, a complex with water is known as a “hydrate”. Solvates of compounds of formula I (including formula A) are within the scope of the invention. It will also be appreciated by those skilled in organic chemistry that many organic compounds can exist in more than one crystalline form. For example, crystalline form may vary from solvate to solvate. Thus, all crystalline forms of the compounds of formula I (including formula A) or the pharmaceutically acceptable solvates thereof are within the scope of the present invention.

The term “pharmaceutically acceptable salts” refers to salt forms that are pharmacologically acceptable and substantially non-toxic to the subject being treated with the compound of the invention. Pharmaceutically acceptable salts include conventional acid-addition salts or base-addition salts formed from suitable non-toxic organic or inorganic acids or inorganic bases. Exemplary acid-addition salts include those derived from inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, sulfamic acid, phosphoric acid, and nitric acid, and those derived from organic acids such as p-toluenesulfonic acid, methanesulfonic acid, ethane-disulfonic acid, isethionic acid, oxalic acid, p-bromophenylsulfonic acid, carbonic acid, succinic acid, citric acid, benzoic acid, 2-acetoxybenzoic acid, acetic acid, phenylacetic acid, propionic acid, glycolic acid, stearic acid, lactic acid, malic acid, tartaric acid, ascorbic acid, maleic acid, hydroxymaleic acid, glutamic acid, salicylic acid, sulfanilic acid, and fumaric acid. Exemplary base-addition salts include those derived from ammonium hydroxides (e.g., a quaternary ammonium hydroxide such as tetramethylammonium hydroxide) those derived from inorganic bases such as alkali or alkaline earth-metal (e.g., sodium, potassium, lithium, calcium, or magnesium) hydroxides, and those derived from non-toxic organic bases such as basic amino acids.

“A pharmaceutically acceptable prodrug” is a compound that may be converted under physiological conditions or by solvolysis to the specified compound or to a pharmaceutically acceptable salt of such compound. “A pharmaceutically active metabolite” refers to a pharmacologically active product produced through metabolism in the body of a specified compound or salt thereof. Prodrugs and active metabolites of a compound may be identified using routine techniques known in the art. See, e.g., Bertolini, G. et al., (1997) J. Med. Chem. 40:2011-2016; Shan, D. et al., J. Pharm. Sci., 86(7):765-767; Bagshawe K., (1995) Drug Dev. Res. 34:220-230; Bodor, N., (1984) Advances in Drug Res. 13:224-331; Bundgaard, H., Design of Prodrugs (Elsevier Press, 1985) and Larsen, I. K., Design and Application of Prodrugs, Drug Design and Development (Krogsgaard-Larsen et al., eds., Harwood Academic Publishers, 1991).

As used herein, some chemical formulas are provided as SMILES using ChemBioDraw Ultra, Version 13 (PerkinElmer). If necessary, the structural formulas and IUPAC chemical names of such SMILES are herein incorporated by reference.

The present invention provides triazine compounds, compositions, and methods of using thereof to treat malaria, chemoprophylaxis, and/or infections by one or more Plasmodium spp. The triazine compounds of the present invention were designed based on exhaustive compound library screening and structure activity relationship (SAR) analysis using in vitro blood stage assays.

A late stage lead compound, described herein as Compound 641, was found to exhibit excellent in vitro potency, desired metabolic stability. Compound 641 produced complete cures (5/5 mice) after a single 160 mg/kg PO dose.

Pharmacokinetic (PK) analysis (80 mg/kg dosed PO, mouse) revealed that Compound 641 possesses a long mouse half-life (8 hr) and good exposure. In the rhesus P. cynomolgi relapsing model (Deye, G; et. al. Am. J. Trop. Med. Hyg., 86(6), 2012, pp. 931-935) Compound 641 prevented malaria parasitemia as a prophylactic drug when dosed once weekly (65 mg, PO) and was well tolerated at 316 mg/kg. Compound 641 exhibits a possible binding affinity to the voltage gated potassium channel encoded by the human Ether-á-go-go-Related Gene (hERG) since the Cmax exceeded the hERG 1050 (600 nM) in an initial hERG assay. See Sanguinetti M, Mitcheson J (2005) Predicting drug-hERG channel interactions that cause acquired long QT syndrome. Trends in Pharmacological Sciences 26: 119-124. Binding to the hERG channel is a well-established in vitro marker for drug induced Torsades de Pointes (TdP). TdP is a rare arrhythmia that can lead to ventricular fibrillation and sudden death. The hERG channel is a large cylindrical cavity with a high density of flat aromatic and polar residues that are highly symmetric. An evaluation of compounds known to bind the hERG channel revealed a pharmacophore with several aromatic (hydrophobic) residues and a basic amine.

Thus, several strategies were used to design triazine compounds exhibiting antimalarial activity and reduced binding affinity to the hERG channel. One approach was to diminish the binding affinity to the hERG channel by disrupting interactions with the polar groups in the channel. To accomplish this, amines were designed encumbered with bulky groups or were designed to have the basic amine contained in a more rigid framework. Another design strategy was to reduce the basicity of the amine to weaken binding in the hERG channel. Another strategy that was employed was to design molecules that contained a polar group (e.g., a hydroxyl (—OH)) to lower the overall lipophilicity and thereby disrupt the binding to the aromatic non-polar surfaces. One unexpected result was that increased steric hindrance on the aryl substituent resulted in reduced hERG channel binding.

Over 760 substituted triazine compounds were designed and profiled in vitro against different drug resistant strains of P. falciparum. Most substituted triazine compounds possessed good in vitro potency (IC50s<500 ng/mL), little evidence of cross-resistance, and a short chemical synthesis (2-4 chemical steps).

Representative compounds were profiled in hERG assays and clear SAR trends were identified with structural modifications that significantly diminish hERG binding, yet have minimal effects on anti-malarial activity. Many compounds in the triazine series of compounds possess an inherently long half-life in animal models, oral efficacy in a Thompson Test (mouse model assay) and may provide effective malaria treatment and prophylaxis at a relatively low cost.

Thus, the compounds of the present invention have the following Formula I:

wherein

R1 is a 5-10 membered aromatic ring having 0-4 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein each substitutable ring nitrogen is independently substituted by —R, or R1 is benzopyan, branched or unbranched —(C₁-C₆)alkyl, or

wherein Y is —CH, —CR, or N;

R2 is a nitrogen attached 5-8 membered monocyclic ring or a nitrogen attached 7-8 membered bicyclo ring system, and further having 0-2 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein and each substitutable ring nitrogen is independently substituted by —R, or R2 is

and

wherein:

L and L′ are each independently a linker selected from the group consisting of a bond, a substituted or unsubstituted —(C₁-C₆)alkyl- which may be branched or unbranched, and

wherein Ring L is a 5-7 membered cyclic or aromatic ring and m and m′ are independently 0-3;

Ra and Ra′ are each independently H or branched or unbranched —(C₁-C₆)alkyl;

Rb and Rb′ are each independently —CO₂R, branched or unbranched —(C₁-C₆)alkyl, branched or unbranched —(C₂-C₈)alkyl substituted with an —OR, —NRR′, or —N(O)RR′ group on one of the C2-C8 carbons, naphthyl, or a 3-7 membered ring having 0-2 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein each substitutable ring nitrogen is independently substituted by —R;

Rc and Rc′ are each independently selected from the group consisting of H, halo, trihalomethyl, trihalomethoxy, branched or unbranched —(C₁-C₆)alkyl, phenyl, branched or unbranched —(C₁-C₆)alkyl-OR, —C(═O)R, —CO₂R, —S(O)₂R, —OR, —NO₂, —CN, —NH₂, —NRR′, —NHC(═O)R, —NHC(OR)═O, —C(O)NRR′, —S(O)_(n)R, and —SO₂NRR′ (wherein NRR′ can form a 4 to 6 member ring), wherein n is 0, 1, or 2; and

R and R′ are each independently H, branched or unbranched —(C₁-C₆)alkyl, branched or unbranched —(C₁-C₆)alkyl alcohol, or —CO₂—(C₁-C₆)alkyl;

wherein where nitrogen is present as a heteroatom, it is at least 2 carbon atoms from any nitrogen atom attached to the triazine ring, and

wherein the ring carbons next to a ring nitrogen are not substituted with —OR, —NO₂, —NH₂, —NRR′, —NHC(O)R, —NHC(O)OR, —S(O)_(n)R, or —SO₂NRR′;

or a pharmaceutically acceptable salt thereof.

In some embodiments of Formula I, R1 is a ring structure selected from the group consisting of naphthyl, biphenyl, and a 5-8 membered aromatic ring, said ring structure having 0-4 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon of said ring structure is independently substituted by —Re, and wherein each substitutable ring nitrogen of said ring structure is independently substituted by —R, or R1 is a branched or unbranched —(C₁-C₆)alkyl, or

wherein Y is —CH, —CR, or N; R2 is a nitrogen attached 5-8 membered monocyclic ring or a nitrogen attached 7-8 membered bicyclo ring system, and further having 0-2 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein and each substitutable ring nitrogen is independently substituted by —R, or R2 is

and wherein: L and L′ are each independently a linker independently selected from the group consisting of a bond, a substituted or unsubstituted —(C₁-C₆)alkyl- which may be branched or unbranched, and

wherein Ring L is a 5-7 membered cyclic or aromatic ring and m and m′ are independently 0-3; Ra and Ra′ are each independently H or a branched or unbranched —(C₁-C₆)alkyl; Rb and Rb′ are each independently a branched —(C₂-C₈)alkyl substituted with an —OR, —NRR′, or —N(O)RR′ group on one of the C2-C8 carbons, or a 3-7 membered ring having 0-2 ring heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein each substitutable ring nitrogen is independently substituted by —R; wherein where nitrogen is present as a heteroatom, it is at least 2 carbon atoms from the nitrogen atom attached to the triazine ring, and wherein the ring carbons next to a ring nitrogen are not substituted with —OR, —NO₂, —NH₂, —NRR′, —NHC(O)R, —NHC(O)OR, —S(O)_(n)R, or —SO₂NRR′; or a pharmaceutically acceptable salt thereof. In some of these embodiments, R2 is selected from the group consisting of R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2. In some of these embodiments, R1 is a 5-8 membered aromatic ring which has at least one substitutable ring carbon substituted with a halo, trihalomethyl, —S(O)₂R, a branched or unbranched —(C₁-C₆)alkyl, or —OR.

In some embodiments of Formula I, R1 is phenyl, naphthyl, biphenyl, pyridyl, quinolinyl, benzopyran,

where z is 0 or 1,

In some embodiments of Formula I, R1 is

In some embodiments of Formula I, R1 is

In some embodiments of Formula I, R2 is selected from the group consisting

wherein x is 1-3 and y is 1-2.

In some embodiments of Formula I, R1 is

and and Rb is selected from the group consisting of

and R2 is

and Rb′ is selected from the group consisting of an amine group,

In some embodiments of Formula I, R1 is phenyl, naphthyl, biphenyl, pyridyl,

and R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2.

In some embodiments of Formula I, R1 is

and Rb is selected from the group consisting of an amine group,

and R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2.

In some embodiments of Formula I, R1 is

and R2 is

and Rb′ is selected from the group consisting of an amine group,

wherein x is 1-3 and y is 1-2.

In some embodiments of Formula I, R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is

In some embodiments of Formula I, R1 is phenyl, naphthyl, biphenyl, or

and R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is

In some embodiments of Formula I, R1 is

and R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is

In some embodiments of Formula I, Rc and Rc′ are each independently selected from the group consisting of t-butyl, Cl, trichloromethyl, F, trifluoromethyl, —CH₃, —NH₂, —NO₂, —(CH₂)NRR′, —NHC(OR)═O, —NHC(═O)R, —NRR′, —OR, —SR, —S(O)R, —S(O)₂R, —COOH, and —COOR. In some embodiments of Formula I, Rc is methyl, t-butyl, halo, trihalomethyl, —S(O)R, —S(O)₂R, —OR, or —COOR. In some embodiments of Formula I, Rc and Rc′ of the R1 group are each independently halo, trihalomethyl or —OR.

In some embodiments of Formula I, R and R′ are each independently selected from the group consisting of H, —CH₃, —C₂H₅, —C₂H₄OH, —CH(CH₃)₂, —CH₂CH(CH₃)₂, and C(═O)OC(CH₃)₃. In some embodiments of Formula I, R is H, methyl, ethyl, —CH₂CH(CH₃)₂, or —(CH₂)OH.

In some embodiments of Formula I, L and L′ are each independently selected from the group consisting of a bond, —CH₂—, —C₂H₄—, —C₃H₆—, —C₄H₈—, —C₅H₁₀—, —CH(CH₃)—, —CH₂CH(CH₃)—, —CH(CH₃)CH₂—, -benzene-, —CH₂-benzene-CH₂—, and -benzene-CH₂—.

Examples of compounds according to the present invention are provided in Table 13. Thus, in some embodiments, the present invention is directed to a compound selected from the group consisting of Ex 1-16 and Compounds 2-745 of Table 13. In some embodiments, the present invention is directed to a compound set forth in Table 13 that exhibits, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, the present invention is directed to a compound set forth in Table 13 that exhibits, in vivo activity, in the Thompson Test, at 160 mg/kg×3 days, preferably 80 mg/kg×3 days, and more preferably 40 mg/kg×3 days, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, the present invention is directed to a compound set forth in Table 13 that exhibits, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and in vivo activity, in the Thompson Test, at 160 mg/kg×3 days, preferably 80 mg/kg×3 days, and more preferably 40 mg/kg×3 days.

In some embodiments, the present invention is directed to a compound set forth in Table 13 that exhibits, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and in vivo activity, in the Thompson Test, at 160 mg/kg×3 days, preferably 80 mg/kg×3 days, and more preferably 40 mg/kg×3 days, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, the present invention is directed to a compound set forth in Table 13 that exhibits in vivo activity in the Rhesus assay.

In some embodiments, the present invention is directed to a compound selected from Table 14. 20. In some embodiments, the present invention is directed to a compound selected from Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and 555. In some embodiments, the present invention is directed to a compound selected from Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and 322.

In some embodiments, the present invention is directed to a pharmaceutical composition comprising one or more compounds of Formula I and pharmaceutically acceptable excipient. In some embodiments, the present invention is directed to a pharmaceutical composition comprising one or more compounds of Table 13, preferably Table 14, and pharmaceutically acceptable excipient. In some embodiments, the present invention is directed to a pharmaceutical composition comprising one or more compounds selected from Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and 555, and pharmaceutically acceptable excipient. In some embodiments, the present invention is directed to a pharmaceutical composition comprising one or more compounds selected from Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and 322, and pharmaceutically acceptable excipient.

It is understood that the structural formulas are intended to represent any configurational form of the depicted compound and is not to be limited merely to a specific compound form depicted by the structural formulas.

Some of the compounds of the present invention may exist as single stereoisomers (i.e., essentially free of other stereoisomers) racemates, or mixtures of enantiomers, diastereomers, or both. All such single stereoisomers, racemates and mixtures thereof are intended to be within the scope of the present invention. Preferably, the inventive compounds that are optically active are used in optically pure form.

Additionally, the structural formulas herein are intended to cover, where applicable, solvated as well as unsolvated forms of the compounds. Also included are miscible formulations of solvate mixtures such as a compound of the invention in combination with an acetone and ethanol mixture. In a preferred embodiment, the solvate includes a compound of the invention in combination with about 20% ethanol and about 80% acetone. Thus, the structural formulas include compounds having the indicated structure, including the hydrated as well as the non-hydrated forms.

Compounds of the present invention that are solids may exist in different crystal or polymorphic forms. Additionally, the compounds of the invention include pharmaceutically acceptable salts, prodrugs, active metabolites, precursors, and salts of such metabolites of the compounds of the present invention.

If the compound of the present invention is a base, the desired pharmaceutically acceptable salt may be prepared by any suitable method available in the art, for example, treatment of the free base with an inorganic acid, such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like, or with an organic acid, such as acetic acid, maleic acid, succinic acid, mandelic acid, fumaric acid, malonic acid, pyrvic acid, oxalic acid, glycolic acid, salicylic acid, a pyranosidyl acid, such as glucuronic acid or galacturonic acid, an α-hydroxy acid, such as citric acid or tartaric acid, an amino acid, such as aspartic acid or glutamic acid, an aromatic acid, such as benzoic acid or cinnamic acid, a sulfonic acid, such as p-toluenesulfonic acid or ethanesulfonic acid, or the like.

If the compound of the present invention is an acid, the desired pharmaceutically acceptable salt may be prepared by any suitable method, for example, treatment of the free acid with an inorganic or organic base, such as an amine (primary, secondary or tertiary) an alkali metal hydroxide or alkaline earth metal hydroxide, or the like. Illustrative examples of suitable salts include organic salts derived from basic amino acids, such as lysine and arginine, ammonia, primary, secondary, and tertiary amines, and cyclic amines, such as piperidine, morpholine and piperazine, and inorganic salts derived from sodium, calcium, potassium, magnesium, manganese, iron, copper, zinc, aluminum and lithium.

The compounds of the present invention may be synthesized using the methods and preparations as follows:

Preparation 1: 4-(4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl)morpholine

Dissolved 2-chloro-4,6-bis(trichloromethyl)-1,3,5-triazine (0.1 g, 0.28 mmol) in THF (1.5 mL). Added morpholine (0.24 mL, 0.29 mmol) and N,N-diisopropylethylamine (0.06 mL, 0.34 mmol) and stirred for 18 h at room temperature. Concentrated and purified by silica gel chromatography eluting with CH₂Cl₂ to obtain the title compound (0.05 g).

Using a similar procedure, the starting triazine of Preparation 1 was treated with the indicated amine in Table 1 to obtain intermediate compounds 1A-1I.

Preparation 2: 2-(p-tolyl)-4,6-bis(trichloromethyl)-1,3,5-triazine

Dissolved aluminum tribromide (1.15 g, 4.3 mmol) and 4-methylbenzonitrile (5.0 g, 43 mmol) in 2,2,2-trichloroacetonitrile (21.5 mL, 215 mmol) and cooled to 0-10° C. under N₂. Bubbled in HCl gas for 2 h. Warned slowly to room temperature and stirred for 18 h. Added acetone (150 mL) and water (50 mL). Extracted the mixture with CH₂Cl₂ (×100 mL). Washed the organic layer with saturated NaHCO₃ (60 mL) and saturated NaCl (60 mL) then dried (Na₂SO₄) and concentrated.

Method 1: Triturated crude product with methanol (150 mL). Filtered to result in a solid, washed with cold methanol (2×15 mL). Dried solid in high vacuum to afford title compound (6.1 g) as a white solid.

Method 2: Dissolved crude product mixture (10 g) in CH₂Cl₂: water [5:1] (60 mL). Added NaOH (1.48 g, 1.5 eq) and heated to 30° C. for 16 h. Cooled the reaction mixture to 23° C. Washed the organic layer with saturated NH₄Cl and saturated NaCl, then dry (Na₂SO₄) and concentrated to obtain the title compound (3.4 g) as a white solid.

Using a similar procedure to Preparation 2, the nitriles in Table 2 were treated by the indicated method for isolation to obtain intermediate compounds 2A-2AF.

Preparation 3: 2-(3-(4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl)phenyl)isoindoline-1,3-dione

Step 1: Dissolved 3-aminobenzonitrile (1.5 g, 12.7 mmol) in anhydrous dioxane (42 mL) under N₂. Added phthalic anhydride (2.54 g, 17.1 mmol). Affixed Dean-Stark trap and refluxed for 16 h. Cooled to 0° C. and filtered off solid (2-((3-cyanophenyl)carbamoyl)benzoic acid). Concentrated filtrate to afford 3-(1,3-dioxoisoindolin-2-yl)benzonitrile (1.6 g) as a white solid. MS, calc'd=248.06. Obsv'd m/z: 248.91 (M+1).

Step 2: The product of Step 1 was treated in a procedure similar to that described in Preparation 2, Method 1, to obtain the title compound as an off-white solid.

Preparation 4: 4-(4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl)phenyl benzoate

Step 1: Treated a solution of 4-hydroxybenzonitrile (5.0 g, 42 mmol) in DMF (20 mL) with 2M KOH (21 mL, 42 mmol) followed by benzyl chloride (3.46 mL, 42 mmol). Heated in an oil bath at 80° C. for 2 h. Cooled to room temperature and poured onto water (100 mL). Filtered the resulting solid, washed with water (2×25 mL) and dried to obtain 4-benzyloxy-benzonitrile (5.1 g) as a solid.

Step 2: Treated the product of Step 1 in a procedure similar to that described in Preparation 2, Method 2 to afford the title compound as a white solid.

Preparation 5: 2-(4-(methylsulfinyl)phenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine

Cooled a solution of the product of Preparation 2G (1.0 g, 2.28 mmol) in CH₂Cl₂ (19.0 mL) to 0° C. and treated with NaHCO₃ (0.38 g, 4.57 mmol). Added mCPBA (77 wt %, 0.56 g, 2.28 mmol) portion-wise. After 20 min at 0° C., added saturated Na₂S₂O₃ (8 mL) and saturated NaHCO₃ (8 mL). Warmed mixture to 23° C. and extract with CH₂Cl₂ (15 mL). Washed the organic layer with saturated NaCl (10 mL) then dried (Na₂SO₄) and concentrated. Purified by flash chromatography (silica gel, eluant: CH₂Cl₂). Combined appropriate fractions and concentrate to give the title compound (0.8 g) as an off-white solid.

Preparation 6: 2-(4-(methylsulfonyl)phenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine

Oxidized the product of Preparation 2G (5.0 g, 11.38 mmol) using a procedure similar to that in Preparation 5 using 4.0 eq. of NaHCO₃ and 2.1 eq. of mCPBA to obtain the title compound as a white solid.

Preparation 7: N-(4-chlorophenyl)-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine

Treated a solution of the product of Preparation 2Z (0.45 g, 1.0 mmol) in THF (3.5 mL) with 4-chloroaniline (0.14 g, 1.14 mmol) and N,N-diisopropylethylamine (0.22 mL, 1.24 mmol). Microwaved solution at 120° C. for 5 min at power of 200 W. Concentrated and purified by silica gel chromatography eluting with hexane followed by CH₂Cl₂ to obtain the title compound (0.3 g).

Using a similar procedure to Preparation 7, the product of Preparation 2Z was treated with the indicated amine in Table 3 to obtain intermediate compounds 7A-7E.

Preparation 8: 2-(tert-butyl)-4,6-dichloro-1,3,5-triazine

Dissolved cyanuric chloride (4.2 g, 22.9 mmol) and CuI (0.22 g, 1.1 mmol) in anhydrous THF (12 mL) and cooled to −10° C. under N₂. Added tert-butylmagnesium chloride (1.0M in THF, 25.4 mL) slowly over 20 min. Added saturated NH₄Cl (5 mL) and warmed reaction to room temperature. Extracted mixture with CH₂Cl₂ (4×75 mL). Washed organic layer with water (35 mL) and saturated NaCl (35 mL) then dried (Na₂SO₄) and concentrated. Purified the product by filtration through a pad of silica gel eluting with CH₂Cl₂ to give the title compound (1.5 g) as a yellow oil.

Table 4 provides a non-limiting list of amines which may be employed to obtain compounds according to the present invention.

Example 1 and Compounds 2-619

N¹-(4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-N²,N²-dimethylpropane-1,2-diamine

Treated a solution of the product of Preparation 2C (0.70 g, 1.5 mmol) in THF (6.0 mL) with N²,N²-dimethylpropane-1,2-diamine (0.18 g, 1.75 mmol). Stirred for 17 h at room temperature. Concentrated and purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.61 g) as a white solid. MS, calc'd=440.98. Obsv'd m/z: 443.10 (M+1).

Using a similar procedure, the appropriate bis-trichloromethyltriazines of Preparations 1-7 were treated with the amines as indicated in Table 5 to obtain Compounds 2-619.

Example 2 and Compounds 620-635

1-(4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)piperidin-4-amine

Step 1: Treated the product of Preparation 2Q (0.10 g, 0.24 mmol) with 4-N-Boc-aminopiperidine (0.054 g, 0.27 mmol) using a procedure similar to that described in Example 1.

Step 2: Treated a solution of the product of Step 1 (0.24 g, 0.49 mmol) in CH₂Cl₂ (1.6 mL) with concentrated trifluoroacetic acid (1.6 mL). Stirred for 12 h at 23° C. Slowly added saturated NaHCO₃ until pH=8. Extracted with CH₂Cl₂ (2 mL). Washed organic layer with saturated NaCl (2 mL) then dried (Na₂SO₄) and concentrated. Purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.05 g) Example 2, as a yellow solid. MS, calc'd=389.04. Obsv'd m/z: 390.27 (M+1).

A procedure similar to that described in Example 2, Steps 1-2, was used with the products of the Preparations as indicated in Table 6 to obtain Compounds 620-635.

Example 3

1-(4-(4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)piperazin-1-yl)ethan-1-one

Step 1: Treated the product of Preparation 2C (0.10 g, 0.22 mmol) with piperazine (0.02 g, 0.24 mmol) using a procedure similar to that described in Example 1.

Step 2: Treated a solution of the product of Step 1 (0.059 g, 0.14 mmol) in CH₂Cl₂ (0.5 mL) with triethylamine (0.03 mL, 0.21 mmol) under N₂. Cooled to 0° C. and added acetyl chloride (0.010 mL, 0.14 mmol) slowly. Warmed mixture to 23° C. and stirred for 1 h, then added water (1 mL). Extracted with CH₂Cl₂ (2×2 mL). Washed organic layer with saturated NaHCO₃ (1 mL) saturated NaCl (1 mL) then dried (Na₂SO₄) and concentrate. Purified the product by filtration through a pad of silica gel eluting with CH₂Cl₂ to give the title compound (0.031 g) as a yellow solid. MS, calc'd=466.96. Obsv'd m/z: (M+1).

Example 4 and Compounds 636-691

N-methyl-4-(4-(methylsulfonyl)phenyl)-N-(2-(pyridin-2-yl)ethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine

Treated a solution of the product of Preparation 6 (0.10 g, 0.21 mmol) in THF (2.1 mL) with N-methyl-2-(pyridin-2-yl)ethanamine (0.35 g, 0.25 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.28 mmol). Stirred for 16 h at room temperature. Concentrated and purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.67 g) as a white solid. MS, calc'd=485.02. Obsv'd m/z: 485.94 (M+1).

Using a similar procedure, the product of the specific Preparations were treated with the indicated amine (in place of N-methyl-2-(pyridin-2-yl)ethanamine in Example 4) in Table 7 to obtain Compounds 636-691.

Example 5 and Compounds 692-704

N-(1-isobutylpiperidin-4-yl)-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine

Cooled a solution of 1-isobutylpiperidin-4-amine 2,2,2-trifluoroacetate (0.04 g, 0.28 mmol) in anhydrous THF (1.0 mL) to 0° C. under N₂ and treated with NaH (60 wt % in mineral oil, 0.17 g, 0.71 mmol). After 5 min at 0° C., the product of preparation 2A (0.10 g, 0.24 mmol) was added and stirred cold for 30 min. Warmed mixture to 23° C. and added saturated NH₄Cl (1 mL) and water (1 mL). Extracted with EtOAc (2×3 mL). Washed organic layer with saturated NaHCO₃ (1 mL) saturated NaCl (1.5 mL) then dried (Na₂SO₄) and concentrate. Purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.021 g) as a gum. MS, calc'd=457.12. Obsv'd m/z: 458.24 (M+1).

Using a similar procedure to Example 5,1-isobutylpiperidin-4-amine 2,2,2-trifluoroacetate was treated with the indicated Preparation product in Table 8 to obtain Compounds 692-704.

Example 6 and Compounds 705-715

tert-butyl 5-(4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Cooled a solution of (1S,4S)-(−)-2-Boc-2,5-diazabicyclo[2.2.1]-heptane (0.05 g, 0.26 mmol) in anhydrous THF (1.0 mL) to 0° C. under N₂ and treat with MeLi (1.7M in hexane, 0.15 mL). After 5 min at 0° C., the product of preparation 2D (0.10 g, 0.24 mmol) was added and stirred cold for 30 min. Warmed mixture to 23° C. and added water (1 mL). Extracted with EtOAc (2×3 mL). Washed organic layer with saturated NaHCO₃ (2 mL) saturated NaCl (2 mL) then dried (Na₂SO₄) and concentrated. Purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.034 g) as an off-white oil. MS, calc'd=503.04. Obsv'd m/z: 504.16 (M+1).

Using a similar procedure, the product of the specific Preparations were treated with the indicated amine in Table 9 to obtain Compounds 705-715.

Example 7 and Compounds 716-726

2-(4-(trichloromethyl)-6-(3-(trifluoromethyl)phenyl)-1,3,5-triazin-2-yl)-2,5-diazabicyclo[2.2.1]heptane

Step 1: Treated (1S,4S)-(−)-2-Boc-2,5-diazabicyclo[2.2.1]-heptane with the product of Preparation 2F using a procedure similar to Example 6.

Step 2: Deprotected the product of Step 1 using a procedure similar to that described in Example 2, Step 2, to afford the title compound as a yellow solid. MS, calc'd=437.02. Obsv'd m/z: 438.20 (M+1).

Using a similar procedure to Example 7, (1S,4S)-(−)-2-Boc-2,5-diazabicyclo[2.2.1]-heptane was treated with the indicated Preparation product in Table 10 to obtain Compounds 716-726.

Example 8 and Compounds 727-742

N²-(2-morpholinophenyl)-N⁴-(3-(pyrrolidin-1-yl)propyl)-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine

Treatment a solution of compound 7E (0.08 g, 0.16 mmol) in THF (1.0 mL) with N-(3-aminopropyl)pyrrolidine (0.02 g, 0.18 mmol) and N,N-diisopropylethylamine (0.04 mL, 0.20 mmol). Microwave solution at 120° C. for 5 min at power of 200 W. Concentrated and purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.02 g) as an off-white oil. MS, calc'd=499.14. Obsv'd m/z: 500.18 (M+1).

Using a similar procedure, the products of the specific Preparations were treated with the indicated amines in Table 11 to obtain Compounds 727-742.

Example 9 and Compounds 743-744

N-(pyridin-4-yl)-4-(trichloromethyl)-6-(4-(trichloromethyl)phenyl)-1,3,5-triazin-2-amine

Treated the product of Preparation 2H (0.38 g, 0.73 mmol) using a procedure similar to that in Example 6 using 2.0 eq. of 4-aminopyridine to obtain the title compound (0.37 g) as an off-white solid.

Using a procedure similar to that described in Example 9, 4-aminopyridine was treated with the products of the Preparations in Table 12 to obtain Compounds 743-744.

Example 10

2-(4-(4-(pyrrolidin-1-yl)phenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-2,5-diazabicyclo[2.2.2]octane hydrochloride

Step 1: Dissolved the product of Preparation 2AA (1.4 g, 3.1 mmol) and 2,5-diazabicyclo[2.2.2]octane-2-carboxylic acid tert butyl ester.HCl (0.76 g, 3.1 mmol) in CH₃CN (25 mL) under N₂. Added DBU (0.91 mL, 6.1 mmol) stirring for 36 h at room temperature. Concentrated and filtered the resulting solid with CH₃CN to afford tert-butyl 5-(4-(4-(pyrrolidin-1-yl)phenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (1.1 g) as a yellow solid.

Step 2: Deprotected a solution of the product of Step 1 (1.1 g, 1.98 mmol) in anhydrous CHCl₃ (18 mL) with 4N HCl in dioxane (18 mL, 71.6 mmol) under N₂. Stirred at room temperature for >18 h, then concentrated. Added diethyl ether (60 mL) and CH₂Cl₂ (5 mL) and stirred for 1 h. Filtered resulting solid, washed with ether and CH₂Cl₂, and dried to give the title compound (0.88 g) as a yellow solid. MS, calc'd=452.10. Obsv'd m/z: 453.10 (M+1).

Example 11

3-(4-((3-(dimethylamino)propyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoic acid

Step 1: Treated the product of Preparation 2AD with N¹,N¹-dimethylpropane-1,3-diamine using a procedure similar to that described in Example 1.

Step 2: Oxidized the product of Step 1 with 0.1 N HCl in diethyl ether using gradual heating. Concentrated to afford the title compound as a white solid which was then free based. Calc'd for C₁₆H₁₈Cl₃N₅O₂: C, 45.89; H, 4.33; N, 16.72. Found: C, 45.88; H, 4.32; N, 16.68.

Example 12

4-(4-(((1-ethylpiperidin-4-yl)methyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoic acid

Step 1: Treated the product of Preparation 2H with (1-ethyl-4-piperidinyl) methanamine using a procedure similar to that described in Example 1.

Step 2: Oxidized the product of Step 1 with aqueous NaOH using gradual heating. Concentrated to afford the title compound as an off-white solid. Calc'd for C₁₉H₂₂Cl₃N₅O₂: C, 47.86; H, 5.07; N, 14.69; Cl, 22.31. Found: C, 48.38; H, 4.72; N, 14.75; Cl, 22.05.

Example 13

N-(4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-N-methylglycine

Step 1: Treated the product of Preparation 2D (0.10 g, 0.24 mmol) with sarcosine tert-butyl ester hydrochloride (0.05 g, 0.26 mmol) using a procedure similar to that described in Example 4, eluting with CH₂Cl₂ during chromatography.

Step 2: Saponified a solution of the product of Step 1 (0.05 g) in CH₂Cl₂ (1.3 mL) with trifluoroacetic acid (0.6 mL) at room temperature. Stirred for 4 h, then concentrated. Added diethyl ether (3 mL). Washed resulting solid with cold diethyl ether (2×2 mL) and dried to afford the title compound (0.03 g) as a white solid. MS, calc'd=393.96. Obsv'd m/z: 394.89 (M+1).

Example 14 and Compound 745

4-((4-((pyridin-2-ylmethyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)amino)phenol

Step 1: Cooled a solution of the product of Preparation 1E (1.0 g, 2.37 mmol) in anhydrous CH₂Cl₂ (2.0 mL) to 0° C. under N₂ and treated with imidazole (0.34 g, 5.1 mmol). After 5 min at 0° C., tert-butylchlorodimethylsilane (0.39 g, 2.60 mmol) was added slowly and warmed to 23° C. Stirred for 1 h, then added saturated NaHCO₃ (1 mL). Extracted with CH₂Cl₂ (2×3 mL). Washed organic layer with saturated NaCl (1.5 mL) then dry (Na₂SO₄) and concentrated. Purified the product by filtration through a pad of silica gel eluting with hexane to give N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine (1.0 g) as a solid.

Step 2: Treated the product of Step 1 (0.11 g, 0.21 mmol) with 2-(aminomethyl)pyridine (0.02 g, 0.23 mmol) using a procedure similar to that described in Example 1.

Step 3: Cooled a solution of the product of Step 2 (0.1 g, 0.19 mmol) in anhydrous THF (1.0 mL) to 0° C. and deprotected with 1.0 M TBAF in THF (0.4 mL) under N₂. Stirred at 0° C. for 5 min, then warmed to room temperature and stirred for 1.5 h. Concentrated and purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.06 g) as a solid. MS, calc'd=410.02. Obsv'd m/z: 411.05 (M+1).

Using a procedure similar to that described in Example 14, 2-(aminomethyl)pyridine in Step 2 was substituted with N-(2-aminoethyl)pyrrolidine to obtain 4-((4-((2-(pyrrolidin-1-yl)ethyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)amino)phenol (Compound 745) as a solid. MS, calc'd=416.07. Obsv'd m/z: 417.04 (M+1).

Example 15

4-(3-aminophenyl)-N-(2-(pyrrolidin-1-yl)ethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine

Step 1: Treated the product of Preparation 3 (0.32 g, 0.60 mmol) with N-(2-aminoethyl)pyrrolidine (0.07 g, 0.66 mmol) using a procedure similar to that described in Example 1.

Step 2: Deprotected a solution of the product of Step 1 (0.18 g, 0.34 mmol) in anhydrous EtOH (2.0 mL) with hydrazine monohydrate (0.45 mL, 27 eq.). Stirred vigorously at room temperature for 16 h. Added 10% aqueous Na₂CO₃ (1.5 mL). Extracted mixture with CH₂Cl₂ (3×5 mL). Washed the organic layer with saturated NaCl (2 mL) dried (Na₂SO₄) and concentrated. Purified by silica gel chromatography eluting with NH₃/MeOH/CH₂Cl₂ mixtures to give the title compound (0.06 g) as a yellow solid. MS, calc'd=400.07. Obsv'd m/z: 401.19 (M+1).

Example 16

1-((4-((3,4-dichlorophenyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)amino)-N,N-dimethylpropan-2-amine oxide

Step 1: Treated the product of Preparation 2C with N²,N²-dimethylpropane-1,2-diamine using a procedure similar to that described in Example 1.

Step 2: Oxidized the product of Step 1 with mCPBA using a procedure similar to that described in Preparation 5 to obtain the title compound as a white solid. Calc'd for C₁₅H₁₇Cl₅N₆O: C, 37.54; H, 3.59; N, 17.40; Cl, 38.16. Found: C, 37.23; H, 3.71; N, 17.40; Cl, 37.86.

The activities of the compounds of the present invention may be measured by any of the methods available to those skilled in the art, including in vitro and in vivo assays. Examples of suitable assays for activity measurements are provided herein. Properties of the compounds of the present invention may be assessed, for example, by using one or more of the assays set out in the Examples below. Other pharmacological methods may also be used to determine the efficacy of the compounds as antiproliferative, antibacterial, antifungal, and antiprotozoal agents. The compounds of the present invention may be used in combination with or as a substitution for known treatments for malaria, chemoprophylaxis, and/or infection by one or more Plasmodium spp.

A compound of the present invention may be administered in a therapeutically effective amount to a subject in need thereof. As used herein, a “subject in need thereof” is one who has or will be exposed to one or more Plasmodium spp. or has been diagnosed as having malaria or being infected with one or more Plasmodium spp. A therapeutically effective amount of one or more compounds of the present invention will vary depending upon factors such as the given compound(s) the pharmaceutical formulation, route of administration, the type of disease or disorder, the degree of the disease or disorder, and the identity of the subject being treated, but can nevertheless be routinely determined by one skilled in the art. Also, as used herein, a “therapeutically effective amount” of a compound of the present invention is an amount which prevents, inhibits, suppresses, or reduces a given clinical condition in a subject as compared to a control. For example, a “therapeutically effective amount” of a compound of the present invention is an amount which prevents, inhibits, suppresses, or reduces malaria (as determined by clinical symptoms or the amount of Plasmodium organisms) in a subject as compared to a control. In some embodiments, a therapeutically effective amount of one or more compounds of the invention ranges from about 0.01 to about 320 mg/kg body weight, preferably about 0.1 to about 160 mg/kg body weight, and more preferably about 0.1 to about 80 mg/kg body weight. The skilled artisan will appreciate that certain factors may influence the dosage required to effectively treat a subject, including but not limited to the severity of the disease or disorder, previous treatments, the general health and/or age of the subject, and other diseases present.

Moreover, treatment of a subject with a therapeutically effective amount of the compound of the present invention may consist of a single administration, or alternatively comprise a series of applications. For example, a subject may be treated with one or more compounds of the present invention at least once. However, the subject may treated with the one or more compounds from about one time per week to about once daily for a given treatment period. The length of the treatment period will depend on a variety of factors such as the severity of the disease or disorder, the concentration and activity of the one or more compounds of the present invention, or a combination thereof. It will also be appreciated that the effective dosage of the one or more compounds used for treatment may increase or decrease over the course of a particular treatment. Changes in dosage may result and become apparent by standard diagnostic assays known in the art. In some instances chronic administration may be required. The compounds of the present invention may be administered before, during, after, or a combination thereof exposure to malaria or Plasmodium spp.

The pharmaceutical formulations of the invention comprise one or more compounds of the present invention and may be prepared in a unit-dosage form appropriate for the desired mode of administration. The pharmaceutical formulations of the present invention may be administered for therapy by any suitable route including oral, rectal, nasal, topical (including buccal and sublingual) vaginal, and parenteral (including subcutaneous, intramuscular, intravenous, and intradermal). It will be appreciated that the preferred route will vary with the condition and age of the recipient, the nature of the condition to be treated, and the given compound(s) of the present invention.

It will be appreciated that the actual dosages of the compounds used in the pharmaceutical formulations of this invention will vary according to the particular compound(s) being used, the particular composition formulated, the mode of administration, and the particular site, host, and disease being treated. Optimal dosages for a given set of conditions may be ascertained by those skilled in the art using conventional dosage determination tests in view of the experimental data for a given compound. Administration of prodrugs may be dosed at weight levels that are chemically equivalent to the weight levels of the fully active forms.

The compounds of the present invention can be incorporated into pharmaceutical formulations suitable for administration. Pharmaceutical formulations of this invention comprise a therapeutically effective amount of one or more compounds of the present invention, and an inert, pharmaceutically or cosmetically acceptable carrier or diluent. As used herein the language “pharmaceutically or cosmetically acceptable carrier” is intended to include any and all solvents, dispersion media, coatings, antibacterial, and antifungal agents, isotonic and absorption delaying agents, and the like, compatible with pharmaceutical or cosmetic administration. The pharmaceutical or cosmetic carrier employed may be either a solid or liquid. Exemplary of solid carriers are lactose, sucrose, talc, gelatin, agar, pectin, acacia, magnesium stearate, stearic acid, and the like. Exemplary of liquid carriers are syrup, peanut oil, olive oil, water, and the like. Similarly, the carrier or diluent may include time-delay or time-release material known in the art, such as glyceryl monostearate or glyceryl distearate alone or with a wax, ethylcellulose, hydroxypropylmethylcellulose, methylmethacrylate, and the like. The use of such media and agents for pharmaceutically or cosmetically active substances is well known in the art.

Except insofar as any conventional media or agent is incompatible with the active compound, use thereof in the formulation is contemplated. Supplementary active compounds can also be incorporated into the formulations. Supplementary active compounds include antibiotics, antiprotozoal agents, antifungal agents, and antiproliferative agents known in the art, analgesics, and other compounds commonly used to treat diseases and disorders associated with cell proliferation, bacterial infection, fungal infection, and protozoal infection.

Antibiotics include penicillin, cloxacillin, dicloxacillin, methicillin, nafcillin, oxacillin, ampicillin, amoxicillin, bacampicillin, azlocillin, carbenicillin, mezlocillin, piperacillin, ticarcillin, azithromycin, clarithromycin, clindamycin, erythromycin, lincomycin, demeclocycline, doxycycline, minocycline, oxytetracycline, tetracycline, quinolone, cinoxacin, nalidixic acid, fluoroquinolone, ciprofloxacin, enoxacin, grepafloxacin, levofloxacin, lomefloxacin, norfloxacin, ofloxacin, sparfloxacin, trovafloxacin, bacitracin, ocolistin, polymyxin B, sulfonamide, trimethoprim-sulfamethoxazole, co-amoxyclav, cephalothin, cefuroxime, ceftriaxone, vancomycin, gentamicin, amikacin, metronidazole, chloramphenicol, nitrofurantoin, co-trimoxazole, rifampicin, isoniazid, pyrazinamide, kirromycin, thiostrepton, micrococcin, fusidic acid, thiolactomycin, fosmidomycin, and the like.

Antiprotozoal agents include chloroquine, doxycycline, mefloquine, metroni dazole, eplornithine, furazolidone, hydroxychloroquine, iodoquinol, pentamidine, mebendazole, piperazine, halofantrine, primaquine, pyrimethamine sulfadoxine, doxycycline, clindamycin, quinine sulfate, quinidine gluconate, quinine dihydrochloride, hydroxychloroquine sulfate, proguanil, quinine, clindamycin, atovaquone, azithromycin, suramin, melarsoprol, eflornithine, nifurtimox, amphotericin B, sodium stibogluconate, pentamidine isethionate, trimethoprim-sulfamethoxazole, pyrimethamine, sulfadiazine, and the like.

Antifungal agents include amphotericin B, fluconazole, itraconazole, ketoconazole, potassium iodide, flucytosine, and the like.

Antiproliferative agents such as altretamine, amifostine, anastrozole, arsenic trioxide, bexarotene, bleomycin, busulfan, capecitabine, carboplatin, carmustine, celecoxib, chlorambucil, cisplatin, cisplatin-epinephrine gel, cladribine, cytarabine liposomal, daunorubicin liposomal, daunorubicin daunomycin, dexrazoxane, docetaxel, doxorubicin, doxorubicin liposomal, epirubicin, estramustine, etoposide phosphate, etoposide VP-16, exemestane, fludarabine, fluorouracil 5-FU, fulvestrant, gemicitabine, gemtuzumab-ozogamicin, goserelin acetate, hydroxyurea, idarubicin, ifosfamide, imatinib mesylate, irinotecan, letrozole, leucovorin, levamisole, liposomal daunorubicin, melphalan L-PAM, mesna, methotrexate, methoxsalen, mitomycin C, mitoxantrone, paclitaxel, pamidronate, pegademase, pentostain, porfimer sodium, streptozocin, talc, tamoxifen, temozolamide, teniposide VM-26, topotecan, toremifene, tretinoin, ATRA, valrubicin, vinorelbine, zoledronate, steroids, and the like.

Toxicity and therapeutic efficacy of such compounds can be determined by standard pharmaceutical procedures in cell cultures or experimental animals, e.g., for determining the LD₅₀ (the dose lethal to 50% of the population) and the ED₅₀ (the dose therapeutically effective in 50% of the population). The dose ratio between toxic and therapeutic effects is the therapeutic index and it can be expressed as the ratio LD₅₀/ED₅₀. Compounds which exhibit large therapeutic indices are preferred. While compounds that exhibit toxic side effects may be used, care should be taken to design a delivery system that targets such compounds to the site of affected tissue in order to minimize potential damage to uninfected cells and, thereby, reduce side effects.

The data obtained from the cell culture assays and animal studies can be used in formulating a range of dosage for use in humans. The dosage of such compounds lies preferably within a range of circulating concentrations that include the ED₅₀ with little or no toxicity. The dosage may vary within this range depending upon the dosage form employed and the route of administration utilized. For any compound used in the method of the invention, the therapeutically effective dose can be estimated initially from cell culture assays. A dose may be formulated in animal models to achieve a circulating plasma concentration range that includes the IC₅₀ (i.e., the concentration of the test compound which achieves a half-maximal inhibition of symptoms) as determined in cell culture. Such information can be used to more accurately determine useful doses in humans. Levels in plasma may be measured, for example, by high performance liquid chromatography.

In Vitro and In Vivo Activity

Various compounds according to the present invention that were synthesized and assayed as described herein and their in vitro and in vivo activities are summarized in Table 13.

SYBR Green Assay In Vitro Assay

The Malaria SYBR Green Fluorescence Assay is a microtiter drug sensitivity assay that uses the intercalation of SYBR Green into malaria DNA as a measure of blood stage Plasmodium falciparum parasite proliferation in the presence of antimalarial compounds. See Johnson, J. D., et al. Assessment and Continued Validation of the Malaria SYBR Green I-Based Fluorescence Assay for Use in Malaria Drug Screening. Antimicrob Agents Chemother. 51:1927, 2007. This assay was performed as a dose response (12 two-fold serial dilutions) to obtain a calculated IC50 determination. A variety of culture adapted P. falciparum strains with different drug resistance properties (including D6, W2, and C235) from geographically diverse areas were used to assay the compounds disclosed herein.

The columns in Table 13 entitled D6, W2, and C235 set forth the IC50's of the indicated compounds in ng/ml against the given strain. In some embodiments, compounds exhibiting IC50's of one or more, preferably two or more strains, more preferably three strains, of about 500 ng/mL or less are preferred. In some embodiments, compounds exhibiting IC50's of one or more, preferably two or more strains, more preferably three strains, of about 150 ng/mL or less are preferred.

HERG Assay

Compounds according to the present invention were tested in the in vitro electrophysiology patch clamp hERG assay known in the art. See M. H. Bridgland-Taylor et al., (2006). Optimisation and validation of a medium-throughput electrophysiology-based hERG assay using IonWorks HT. Journal of Pharmacological and Toxicological Methods. 54, 189-199. The hERG patch clamp assay is an automated patch-clamp electrophysiology assay for hERG blocking where the membrane potential is controlled across the cell membrane. Compounds were tested to assess their inhibition of current of the hERG potassium ion channel relative to control. The control was quinidine. Results are reported as % inhibition at 10 μM in Table 13. In some embodiments, compounds exhibiting hERG activity of about 75% inhibition or less at 10 μM are preferred. In some embodiments, compounds exhibiting hERG activity of about 50% inhibition or less at 10 μM are preferred. In some embodiments, compounds exhibiting hERG activity of about 40% inhibition or less at 10 μM are preferred. In some embodiments, compounds exhibiting hERG activity of about 30% inhibition or less at 10 μM are preferred.

In Vitro Cytotoxicity Assay

The In vitro Cytotoxicity Assay is a colorimetric microtiter drug toxicity assay that uses the ability of a cell to convert a tetrazolium salt, MTT, (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium) to insoluble formazan dyes as a measure of cellular cytotoxicity. See Ferrari, M., et al. MTT colorimetric assay for testing macrophage cytotoxic activity in vitro. J Immunol Methods 1990 Aug. 7; 131(2):165-72. The ability of a cell to reduce MTT is dependent on functioning mitochondria, and toxic compounds affecting mitochondrial function result in impaired production of the reduced purple formazan dye. This assay was conducted as a singlet dose response (11 two-fold serial dilutions) utilizing HepG2 liver cells in the presence of experimental compounds to obtain a calculated IC50 determination.

All compounds tested did not exhibit any significant cytotoxicity.

Thompson Test—In Vivo Mouse Assay

The Modified Thompson mouse malaria assay is an in vivo rodent assay. See Ager, A. L. Experimental models: Rodent Malaria Models (in vivo) p. 225-254. In W. Peters and W. H. G. Richards (ed.) Handbook of experimental pharmacology: Antimalarial Drugs, vol. 68. Springer-Verlag, New York, N.Y. 1984. This assay was used to measure the survivability of mice and parasite clearance following administration of the compounds of the present invention 3 days after a blood stage lethal dose of P. berghei was administered on Day 0. Five mice (ICR strain) were used for each compound dose group (dosed on days 3, 4, and 5) and 10 ICR mice were used for controls (vehicle). The percentage of parasitemia was measured routinely throughout the 30-day experiment by a flow cytometry method that measures malaria blood stage parasitemia by intercalation of the fluorescent dye YOYO 1. The survivability of the mice was determined by core body temperature and body weight changes. The endpoints of this assay include no clinical indications of disease and a negative parasitemia on day 31 post-infection, which is designated as a “cure”. Untreated control died on Day 7. Compounds extending a subject's lifespan to Day 14 were indicated as suppressive. Typically, 6 dosing groups were used in each experiment, which assess 6 compound dose groups requiring 40 mice per experiment (6 compound dosing groups plus controls).

Not all synthesized compounds were subjected to the Thompson Test. Table 14 summarizes the results of the compounds that were tested. As shown in Table 14, (40×3), (80×3), and (160×3) indicates administration of the given compound at 40 mg/kg for 3 days, 80 mg/kg for 3 days, and 160 mg/kg for 3 days, respectively. Cures indicates mice survive till the end of study (30 days); suppressive, indicates mice survive more than two fold (days) compared to negative control group.

In some embodiments, compounds exhibiting in vivo activity at 160 mg/kg×3, are preferred. In some embodiments, compounds exhibiting in vivo activity at 80 mg/kg×3, are preferred. In some embodiments, compounds exhibiting in vivo activity at 40 mg/kg×3, are preferred.

Rhesus Assay

The Rhesus Antimalarial Drug Screening model is an in vivo assay which measures liver stage activity of drugs against P. cynomolgi, a relapsing primate malaria parasite. The assay system involves establishing a liver stage malaria infection via injection of P. cynomolgi sporozoites. Testing of both liver stage activity, radical cure activity, and blood schizonticidal activity is possible in this model with varying dosing schedules and partner drugs. See Deye, G; et. al. Am. J. Trop. Med. Hyg., 86(6), 2012, pp. 931-935. Malaria prophylaxis indicates monkey was free of clinical signs of malaria during testing duration; malaria cures indicate monkeys were free of blood stage parasites at end of treatment regimen.

Due to expense, not all synthesized compounds were subjected to the Rhesus Assay. Table 14 summarizes the results of the compounds that were tested.

In some embodiments, compounds exhibiting in vivo activity in the Rhesus assay are preferred.

In some embodiments, preferred compounds according to the present invention exhibit, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, preferred compounds according to the present invention exhibit in vivo activity, in the Thompson Test, at 160 mg/kg×3, preferably 80 mg/kg×3, and more preferably 40 mg/kg×3, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, preferred compounds according to the present invention exhibit, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and in vivo activity, in the Thompson Test, at 160 mg/kg×3, preferably 80 mg/kg×3, and more preferably 40 mg/kg×3.

In some embodiments, preferred compounds according to the present invention exhibit, in the SYBR Green Assay, IC50's against at least one, preferably two or more, more preferably three or more Plasmodium strains, of about 500 ng/mL or less, preferably 150 ng/mL or less, and in vivo activity, in the Thompson Test, at 160 mg/kg×3, preferably 80 mg/kg×3, and more preferably 40 mg/kg×3, and hERG activity of about 75% inhibition or less, preferably 50% inhibition or less, more preferably about 40% inhibition or less, and most preferably about 30% inhibition or less at 10 μM.

In some embodiments, preferred compounds according to the present invention exhibit in vivo activity in the Rhesus assay.

In some embodiments, preferred compounds according to the present invention are compounds set forth in Table 14.

In some embodiments, preferred compounds are compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and 555. In some embodiments, preferred compounds are compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and 322.

As provided herein, the compounds of the present invention are useful in the treatment of malaria, chemoprophylaxis, and/or infection by one or more Plasmodium spp. In some embodiments, the Plasmodium spp. is selected from the group consisting of D6, W2, C235, and C2B. In some embodiments, the Plasmodium spp. is a drug resistant strain. In some embodiments, the subject is a mammal, preferably a human. In some embodiments, the subject is a human. In some embodiments, the subject is in need thereof. As used herein, a “subject in need” is one who has been diagnosed as having or suffers from malaria or will likely be exposed to Plasmodium spp.

In some embodiments, the subject is administered a therapeutically effective amount of one or more compounds, preferably one or more preferred compounds, according to the present invention, more preferably one or more compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and 555, and most preferably one or more compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and 322. In some embodiments, the subject is treated before, during, and/or after exposure to one or more Plasmodium spp.

In some embodiments, the present invention is directed to a method of malaria, providing chemoprophylaxis, and/or treating or inhibiting an infection by one or more Plasmodium spp. in a subject which comprises, consists essentially of, or consists of administering a therapeutically effective amount of one or more compounds, preferably one or more preferred compounds according to the present invention, more preferably one or more compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and 555, and most preferably one or more compounds selected from the group consisting of 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and 322, or compositions thereof. In some embodiments, the therapeutically effective amount is administered as a single dose or as multiple doses over a period of time.

In some embodiments, the present invention is directed to the use of one or more compounds, preferably one or more preferred compounds according to the present invention, or compositions thereof for treating malaria, providing chemoprophylaxis, and/or treating or inhibiting an infection by one or more Plasmodium spp.

In some embodiments, the present invention is directed to the use of one or more compounds, preferably one or more preferred compounds according to the present invention, or compositions thereof for the manufacture of a medicament for treating malaria, providing chemoprophylaxis, and/or treating or inhibiting an infection by one or more Plasmodium spp.

In some embodiments, the present invention is directed to the use of one or more compounds, preferably one or more preferred compounds according to the present invention, or compositions thereof for the manufacture of a medicament for treating malaria, providing chemoprophylaxis, and/or treating or inhibiting an infection by one or more Plasmodium spp., wherein the medicament is prepared to be administered in a therapeutically effective amount.

TABLE 1 Cmpd SMILES Amine 1A ClC(C1═NC(NC2═CC═CN═C2OC)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2-methoxypyridin-3-amine 1B ClC(C1═NC(NC2═CC═C(OC)N═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 6-methoxypyridin-3-amine 1C ClC(C1═NC(NC2═CC═C(Cl)C(Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 3,4-dichloroaniline 1D FC(F)(F)OC1═CC═C(NC2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)C═C1 4-(trifluoromethoxy)aniline 1E OC1═CC═C(NC2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)C═C1 4-aminophenol 1F ClC(C1═NC(NC2═CC(Cl)═CC(Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 3,5-dichloroaniline 1G ClC(C1═NC(NC2═CC═CC═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl aniline 1H ClC(C1═NC(NC2═CC═C3C═CC═CC3═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl naphthylamine 1I FC(C1═CC(NC2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)═CC═Cl)(F)F 3-(trifluoromethyl)aniline

TABLE 2 Cmpd SMILES Method Nitrile 2A ClC(C1═NC(C2═CC═CC(OC)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 3-methoxybenzonitrile 2B ClC(C1═NC(C2═CC═C(OC)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-methoxybenzonitrile 2C ClC(C1═NC(C2═CC═C(Cl)C(Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 3,4-dichlorobenzonitrile 2D ClC(C1═NC(C2═CC═C(CDC═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-chlorobenzonitrile 2E ClC(C1═NC(C2═CC═C(C(C)(C)C)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-(tert-butyl)benzonitrile 2F FC(C1═CC(C2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)═CC═Cl)(F)F 1 3-(trifluoromethyl)benzonitrile 2G ClC(C1═NC(C2═CC═C(SC)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-(methylthio)benzonitrile 2H ClC(C1═CC═C(C2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)C═C1)(Cl)Cl 1^(a) 4-(trichloromethyl)benzonitrile 2I ClC(C1═NC(C2═CC═CC═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 benzonitrile 2J ClC(C1═NC(C2═CC═C3C═CC═CC3═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1^(b) 2-naphthonitrile 2K ClC(C1═NC(C2═CC═CC═C2C)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 2-methylbenzonitrile 2L ClC(C1═NC(C2═CC(Cl)═CC(Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 3 ,5-dichlorobenzonitrile 2M ClC(C1═NC(C2═CC═C(C3═CC═CC═C3)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)C1 1 [1,1′-biphenyl]-4-carbonitrite 2N ClC(C1═NC(C2═CC═CC([N+]([O−])═O)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 2-nitrobenzonitrile 2O ClC(C1═NC(C2═CC═CC═C2C3═CC═C(C)C═C3)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4′-methyl-[1,1′-biphenyl]-2- carbonitrile 2P ClC(C1═NC(C2═CC═CC(Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 3-chlorobenzonitrile 2Q ClC(C1═NC(C2═CC═C(F)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-fluorobenzonitrile 2R ClC(C1═NC(C2═C3C═CC═CC3═C(OC)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 4-methoxy-1-naphthonitrile 2S ClC(C1═NC(C2═CC═C(OC)C(OC)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 3,4-dimethoxybenzonitrile 2T ClC(C1═NC(C2═CC(OC)═CC(OC)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 3,5-dimethoxybenzonitrile 2U ClC(C1═NC(C2═CC(C═CC(C)(C)O3)═C3C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 2,2-dimethyl-2H-chromene-6- carbonitrile 2V ClC(C1═NC(C2═CC═CC═C2OC)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 2-methoxybenzonitrile 2W ClC(C1═NC(CC2═CC═CC═C2OC)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 2-(2- methoxyphenyl)acetonitrile 2X ClC(C1═NC(CC2═CC═C(OC)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 2-(4- methoxyphenyl)acetonitrile 2Y ClC(C1═NC(CC2═CC═CC(OC)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 2-(3- methoxyphenyl)acetonitrile 2Z ClC(C1═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1 trichloroacetonitrile 2AA ClC(C1═NC(C2═CC═C(N3CCCC3)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 1^(c) 4-(pyrrolidin-1-yl)benzonitrile 2AB O═C(OCC)C1═CC═C(C2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)C═C1 1 ethyl 4-cyanobenzoate 2AC FC(C1═CC═C(C2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)C═C1)(F)F 2 4-(trifluoromethyl)benzonitrile 2AD ClC(C1═CC(C2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)═CC═Cl)(Cl)Cl 2 3-(trichloromethyl)benzonitrile 2AE ClC(C1═NC(C2═CC(C(F)(F)F)═CC(C(F)(F)F)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 3,5- bis(trifluoromethyl)benzonitrile 2AF ClC(C1═NC(C2═CC(C(Cl)(Cl)Cl)═CC(C(Cl)(Cl)Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2 3,5- bis(trichloromethyl)benzonitrile ^(a)substitute acetonitrile for methanol ^(b)substitute diethyl ether for methanol ^(c)substitute CH₂Cl₂ for methanol

TABLE 3 Cmpd SMILES Amine 7A CC(NC1═CC═CC(NC2═NC(C(Cl)(Cl)Cl)═NC(C(Cl)(Cl)Cl)═N2)═C1)═O N¹-(3-aminophenyl)acetamide 7B ClC(C1═NC(NC2═CC═C(N3CCN(C)CC3)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 4-(4-methylpiperazino)aniline 7C ClC(C1═NC(NC2═CC═C(N3N═CC═C3)C═C2)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 4-(1H-pyrazol-1-yl)aniline 7D ClC(C1═NC(NC2═CC═CC═C2OC)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl 2-methoxyaniline 7E ClC(C1═NC(NC2═CC═CC═C2N3CCOCC3)═NC(C(Cl)(Cl)Cl)═N1)(Cl)Cl) 2-morpholinoaniline

TABLE 4 Amine Chemical Name A1 N-(2-aminoethyl)pyrrolidine A2 N-(3-aminopropyl)pyrrolidine A3 2-(2-aminoethyl)-1-methylpyrrolidine A4 N,N-diethylethylenediamine A5 2-(pyrazin-2-yl)ethanamine A6 (1S,4S)-(-)-2-Boc-2,5-diazabicyclo[2.2.1]-heptane A7 homopiperazine A8 N-methyl-homopiperazine A9 piperazine A10 1-methylpiperazine A11 1,2-diamino-2-methylpropane A12 4-amino-1-methyl-piperidine A13 2-methoxypyridin-3-amine A14 4-N-Boc-aminopiperidine A15 4-piperidinamine A16 (1-ethyl-4-piperidinyl)methanamine A17 1-ethyl-3-piperidinamine A18 4-aminopyridine A19 N-methyl-2-(pyridin-4-yl)ethanamine A20 morpholine A21 2-(piperazin-1-yl)ethanol A22 1-(1-ethylpiperidin-4-yl)ethanamine A23 2-(1,4-diazepan-1-yl)ethanol A24 N¹,N¹-dimethylpropane-1,3-diamine A25 1-isobutylpiperidin-4-amine A26 4-(aminomethyl) oxan-4-amine A27 3-(aminomethyl) pentan-3-amine A28 1-(aminomethyl) cyclohexan-1-amine dihydrochloride A29 1-(aminomethyl) cyclopentan-1-amine dihydrochloride A30 1-(aminomethyl) cyclopropan-1-amine dihydrochloride A31 4-Amino-2,2,6,6-tetramethylpiperidine A32 (1-isopropylpiperidin-4-yl)methanamine A33 (1-methylpiperidin-4-yl)methanamine A34 3-N-Boc-amino-azetidine A35 4-(aminomethyl)pyridine A36 3-picolylamine A37 2-(aminomethyl)pyridine A38 2-pyridin-4-yl-ethylamine A39 3-(2-aminoethyl)pyridine A40 2-(2-aminoethyl)pyridine A41 2-morpholinoaniline A42 4-(1H-pyrazol-1-yl)aniline A43 4-(4-methylpiperzino)aniline A44 N¹-(3-aminophenyl)acetamide A45 2-((2-aminoethyl)thio)ethanol A46 (1,3-dimethyl-1H-pyrazol-5-yl)methanamine A47 N,N-dimethylpyrrolidin-3-amine A48 3-(azepan-1-yl)-2,2-dimethylpropan-1-amine A49 N-methyl-N-(2-pyridin-3-ylbenzyl)amine A50 3-aminopyridine A51 3,4-dichlorophenylaniline A52 (3-(pyrrolidin-1-ylmethyl)phenyl)methanamine A53 piperidine-4-carboxamide A54 N²,N²-dimethylpropane-1,2-diamine A55 N¹,N¹-dimethylpropane-1,2-diamine A56 2-morpholinoethanamine A57 ethanolamine A58 N,N-dimethylpiperidin-3-amine A59 N-(2-hydroxyethyl)ethylenediamine A60 cyclohexane-1,2-diamine A61 sarcosine tert-butyl ester hydrochloride A62 5-(Pyrrolidin-l-yl)pentan-1-amine A63 N¹,N¹-Diethylpropane-1,3-diamine A64 (1-ethylpyrrolidin-3-yl)methanamine A65 1-(1-methylpiperidin-2-yl)methanamine A66 N,N-Dimethylcyclohexane-1,4-diamine A67 (3-aminobutyl)diethylamine A68 (2-aminopropyl)diethylamine A69 4-Amino-1-diethylaminopentane A70 N-methyl-2-(pyridin-2-yl)ethanamine A71 N¹,N¹-diethylcyclohexane-1,3-diamine A72 N¹,N¹-dipropylpropane-1,2-diamine

TABLE 5 MS, found (M + 1) or Cmpd SMILES Prep Amine MS, calc'd mp ( ° C. ) 2 CC(CN(C)C)Nc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A55 440.98 442.31 3 CN(C)C1CCN(C1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A47 453.05 454.16 4 FC(F)(F)c1cccc(c1)c2nc(NCCN3CCOCC3)nc(n2)C(Cl)(Cl)Cl 2F A56 469.05 470.21 5 FC(F)(F)c1cccc(c1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2F A1 453.05 454.41 6 COc1cccc(c1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2A A2 429.09 430.22 7 COc1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2B A2 429.09 430.36 8 CN(C)C1CCCN(C1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A58 467.07 468.17 9 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCC(C3)N(C)C 2B A47 415.07 416.24 10 CN(C)C1CCN(C1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A47 419.02 420.35 11 CCOC(═O)c1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AB A1 457.08 458.28 12 CCOC(═O)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AB A2 471.10 472.29 13 CCOC(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCC(C3)N(C)C 2AB A47 457.08 458.21 14 CCOC(═O)c1ccc(cc1)c2nc(NCC(C)(C)N)nc(n2)C(Cl)(Cl)Cl 2AB A11 431.07 432.17 15 CCOC(═O)c1ccc(cc1)c2nc(NCCN(CC)CC)nc(n2)C(Cl)(Cl)Cl 2AB A4 459.10 460.23 16 CCOC(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2AB A10 443.07 444.24 17 CCOC(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCNCC3 2AB A9 429.05 430.32 18 Clc1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2D A1 419.02 420.20 19 Clc1ccc(cc1Cl)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2C A1 452.98 454.32 20 CN(C)C1CCN(C1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A47 452.98 454.53 21 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A11 426.97 428.27 22 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A10 438.97 440.28 23 CN(CCc1ccncc1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A19 474.97 25 Clc1ccc(cc1Cl)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCNCC3 2C A9 424.95 26 Clc1ccc(cc1Cl)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2C A35 446.94 27 COc1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2B A1 415.07 28 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCNCC3 2B A9 387.04 388.22 29 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A10 405.01 406.00 30 OCCSCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A45 459.93 31 Clc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCOCC3 2D A20 391.98 393.07 32 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A10 427.11 428.22 33 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(C)(C)C 2E A4 443.14 444.16 34 CC(C)(C)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2E A2 455.14 456.29 35 ClC(Cl)(Cl)c1nc(NCCN2CCCC2)nc(n1)c3ccc(OCc4ccccc4)cc3 4 A1 491.10 492.19 36 ClC(Cl)(Cl)c1nc(NCCCN2CCCC2)nc(n1)c3ccc(OCc4ccccc4)cc3 4 A2 491.10 492.12 37 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(OCc4ccccc4)cc3)CC1 4 A16 519.14 520.29 38 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C)CC1 6 A16 491.07 492.00 39 CS(═O)(═O)c1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 6 A1 463.04 464.00 40 OCCN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A21 435.02 435.90 41 COc1cccc(c1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(CCO)CC3 2A A21 431.07 432.15 42 OCCN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A21 469.05 470.00 43 COc1cccc(c1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2A A10 401.06 402.00 44 CSc1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2G A2 445.07 446.29 45 CSc1ccc(cc1)c2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl 2G A3 445.07 446.00 46 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A3 455.14 456.92 47 CSc1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2G A1 431.05 432.18 48 CSc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2G A10 449.02 450.05 49 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(SC)cc2 2G A4 433.07 434.12 50 Cc1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2 A1 399.08 400.11 51 Cc1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2 A2 413.09 414.13 52 CN1CCCC1CCNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C)C═C1 2 A3 413.09 414.49 53 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)(Cl))c2ccc(C)cc2 2 A4 415.02 416.15 54 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A10 449.02 450.07 55 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(Cl)(Cl)Cl 2H A11 474.95 476.22 56 CN(C)C1CCN(C1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A47 500.96 502.08 57 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2H A3 500.96 502.02 58 CS(═O)(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCOCC3 6 A20 435.99 437.15 59 CCN(CC)CCNc1nc(Cc2ccc(OC)cc2)nc(n1)C(Cl)(Cl)Cl 2X A4 431.10 432.02 60 COc1ccc(Cc2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl)cc1 2X A2 443.10 444.00 61 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A12 500.96 501.97 62 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A8 500.96 501.89 63 COc1ccccc1Nc2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl 7D A3 444.10 446.43 64 CN1CCCC1CCNc2nc(Nc3ccccc3N4CCOCC4)nc(n2)C(Cl)(Cl)Cl 7E A3 499.14 500.31 65 COc1ccccc1Nc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 7D A10 416.07 418.25 66 COc1ccccc1Nc2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 7D A1 430.08 432.42 67 COc1ccccc1Nc2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 7D A2 444.10 446.38 68 COc1ccccc1Cc2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2W A2 443.10 444.02 69 COc1ccccc1Cc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2W A10 415.07 415.98 70 CCN(CC)CCNc1nc(Cc2ccccc2OC)nc(n1)C(Cl)(Cl)Cl 2W A4 431.10 432.13 71 COc1ccccc1Cc2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl 2W A3 443.10 444.04 72 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)C 5 A10 433.03 433.94 73 CN1CCCC1CCNc2nc(Nc3ccc(cc3)n4cccn4)nc(n2)C(Cl)(Cl)Cl 7C A3 480.11 481.50 74 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)S(═O)(═O)C 6 A4 465.06 466.29 75 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A3 477.06 478.09 76 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A8 463.04 464.00 77 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A12 463.04 463.99 78 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3 2I A17 399.08 400.07 79 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A17 455.14 456.22 80 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(C)cc3 2 A17 413.09 414.05 81 CCN1CCCC(C1)Nc2nc(Cc3ccc(OC)cc3)nc(n2)C(Cl)(Cl)Cl 2X A17 443.10 444.02 82 COc1cccc(Cc2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl)c1 2Y A1 429.09 430.11 83 COc1cccc(Cc2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl)c1 2Y A2 443.10 444.05 84 COc1cccc(Cc2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl)c1 2Y A3 443.10 444.12 85 CCN1CCCC(C1)Nc2nc(Cc3cccc(OC)c3)nc(n2)C(Cl)(Cl)Cl 2Y A17 443.10 444.02 86 CCN1CCCC(C1)Nc2nc(Cc3ccc(OC)cc3)nc(n2)C(Cl)(Cl)Cl 2X A17 443.10 444.02 87 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A17 477.06 477.98 88 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(SC)cc3 2G A17 445.07 446.36 89 COc1ccc(Cc2nc(NCCN3CCCC3C)nc(n2)C(Cl)(Cl)Cl)cc1 2X A3 443.10 444.24 90 COc1ccc(Cc2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl)cc1 2X A1 429.09 430.01 91 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A3 433.04 434.17 92 CN1CCCC1CCNc2nc(Nc3cccc(NC(═O)C)c3)nc(n2)C(Cl)(Cl)Cl 7A A3 471.11 472.34 93 CS(═O)(═O)c1ccc(cc1)c2nc(Nc3ccncc3)nc(n2)C(Cl)(Cl)Cl 6 A18 442.98 444.25 94 CCN1CCCC(C1)Nc2nc(Cc3ccccc3OC)nc(n2)C(Cl)(Cl)Cl 2W A17 443.10 444.03 95 CS(═O)(═O)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 6 A3 477.06 478.02 96 CS(═O)(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 6 A7 449.02 449.98 97 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)S(═O)(═O)C 6 A11 437.02 438.11 98 CS(═O)(═O)c1ccc(cc1)c2nc(NCCNCCO)nc(n2)C(Cl)(Cl)Cl 6 A59 453.02 453.95 99 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A10 486.95 487.86 100 COc1cccc(c1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2A A7 401.06 402.23 101 COc1cc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2B A7 401.06 402.28 102 Cc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2 A7 385.06 386.06 103 Clc1ccc(cc1Cl)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2C A7 438.97 439.99 104 COc1ccccc1c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2V A1 415.07 416.11 105 COc1ccccc1c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2V A2 429.09 430.31 106 COc1ccccc1c2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl 2V A3 429.09 430.08 107 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccccc2OC 2V A4 417.09 418.08 108 FC(F)(F)c1cccc(c1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2F A7 439.03 440.38 109 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A8 453.05 454.12 110 COc1cccc(c1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCN(C)CC3 2A A8 415.07 416.23 111 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCN(C)CC3 2B A8 415.07 416.19 112 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(C)cc3 2 A8 399.08 400.17 113 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A8 452.98 454.09 114 COc1ccccc1c2nc(NC3CCN(C)CC3)nc(n2)C(Cl)(Cl)Cl 2V A12 415.07 416.12 115 CC(C)(C)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2E A9 427.11 428.10 116 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A12 441.13 442.41 117 CC(C)(C)c1ccc(cc1)c2nc(NCC(C)(C)N)nc(n2)C(Cl)(Cl)Cl 2E A11 415.11 416.55 118 CS(═O)(═O)c1ccc(cc1)c2cc(cc(c2)C(Cl)(Cl)Cl)N3CCN(CCO)CC3 6 A21 479.04 480.05 119 OCCN1CCN(c2nc(C(Cl)(Cl)Cl)nc(c3ccc(C(Cl)(Cl)Cl)cc3)n2)CC1 2H A21 516.96 518.09 120 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A8 441.13 442.16 121 Cc1ccccc1c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2K A1 399.08 400.03 122 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3C 2K A3 413.09 414.06 123 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccccc2C 2K A4 401.09 402.04 124 Cc1ccccc1c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2K A7 385.06 386.01 125 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3C 2K A8 399.08 400.04 126 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3C 2K A12 399.08 400.05 127 OCCN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A23 530.97 532.08 128 Cc1ccccc1c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2K A2 413.09 414.06 129 CN(Cc1ccccc1c2cccnc2)c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)S(═O)(═O)C 6 A49 547.04 548.12 130 COc1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2B A35 409.03 410.67 131 CC(C)(C)c1nc(NCc2ccncc2)nc(n1)C(Cl)(Cl)Cl 8 A35 359.05 132 CS(═O)(═O)c1nc(nc(n1)C(Cl)(Cl)Cl)N2CCCN(CCO)CC2 6 A23 493.05 494.25 133 COc1ccccc1Cc2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2W A35 423.04 424.11 134 Cc1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2 A35 393.03 394.41 135 COc1ccccc1c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2V A35 409.03 410.12 136 Clc1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2D A35 412.98 414.64 137 CC(C)(C)c1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2E A35 435.08 436.25 138 FC(F)(F)c1cccc(c1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2F A35 447.00 448.07 139 Clc1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2D A38 426.99 428.01 140 Clc1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2D A40 426.99 428.06 141 Clc1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2D A37 412.98 414.05 142 Clc1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2D A36 412.98 414.07 143 Clc1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2D A39 426.99 428.01 144 COc1ccccc1Cc2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2W A39 437.06 438.05 145 Cc1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2 A38 407.05 408.08 146 COc1ccccc1c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2V A38 423.04 424.17 147 COc1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2B A38 423.04 424.09 148 CC(C)(C)c1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2E A38 449.09 446.94 149 FC(F)(F)c1cccc(c1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2F A38 461.02 462.56 150 CSc1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2G A38 439.02 440.03 151 COc1cccc(c1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2A A38 423.04 424.41 152 COc1ccccc1Cc2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2W A36 423.04 424.10 153 Cc1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2 A36 393.03 394.21 154 COc1ccccc1c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2V A36 409.03 410.10 155 COc1cccc(c1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2S A36 409.03 410.02 156 COc1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2B A36 209.03 410.04 157 Clc1ccc(cc1Cl)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2C A36 446.94 448.00 158 CC(C)(C)c1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2E A36 435.08 436.17 159 FC(F)(F)c1cccc(c1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2F A36 447.00 448.05 160 CSc1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2G A36 425.00 426.03 161 CC(C)(C)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCNCC3 2E A9 413.09 414.12 162 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2H A39 508.93 509.85 163 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2H A40 508.93 510.18 164 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2H A36 494.91 496.00 165 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2H A37 493.92 495.96 166 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2H A38 508.93 509.90 167 Cc1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2 A37 393.03 394.10 168 COc1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2B A37 409.03 410.13 169 Clc1ccc(cc1Cl)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2C A37 446.94 447.96 170 CC(C)(C)c1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2E A37 435.08 436.18 171 FC(F)(F)c1cccc(c1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2F A37 447.00 448.02 172 Cc1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2 A39 407.05 408.08 173 COc1cccc(c1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2A A39 423.04 424.17 174 COc1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2B A39 423.04 424.12 175 CC(C)(C)c1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2E A39 449.09 450.12 176 Clc1ccc(cc1Cl)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2C A38 460.95 461.96 177 CS(═O)(═O)c1ccc(cc1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 6 A37 456.99 458.08 178 CS(═O)(═O)c1ccc(cc1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 6 A38 471.01 472.06 179 CS(═O)(═O)c1ccc(cc1)c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 6 A39 471.01 472.04 180 CS(═O)(═O)c1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 6 A40 471.01 472.10 181 COc1ccccc1c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2V A37 409.03 410.07 182 COc1ccccc1c2nc(NCCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2V A39 423.04 424.17 183 COc1ccccc1c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2V A40 423.04 424.14 184 COc1cccc(c1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2A A40 423.04 424.29 185 COc1ccc(cc1)c2nc(NCCc3ccccn3)ne(n2)C(Cl)(Cl)Cl 2B A40 423.04 424.12 186 FC(F)(F)c1cccc(c1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2F A40 461.02 462.03 187 CSc1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2G A40 439.02 440.12 188 ClC(Cl)(Cl)c1nc(NCCc2ccccn2)nc(n1)c3ccccc3 2I A40 393.03 394.49 189 Cc1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2 A40 407.05 408.09 190 Clc1ccc(cc1Cl)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2C A40 460.95 462.15 191 CC(C)(C)c1ccc(cc1)c2nc(NCCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2E A40 449.09 450.17 192 COc1cccc(c1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2A A1 415.07 416.18 193 COc1cccc(c1)c2nc(NC3CCN(C)CC3)nc(n2)C(Cl)(Cl)Cl 2A A12 415.07 416.12 194 CC(C)(C)OC(═O)NC1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A14 587.00 587.83 195 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(Cl)cc(Cl)c2 2L A11 426.97 428.73 196 ClC(Cl)(Cl)c1nc(NCCN2CCCC2)nc(n1)c3ccc(cc3)c4ccccc4 2M A1 461.09 462.80 197 ClC(Cl)(Cl)c1nc(NCCCN2CCCC2)nc(n1)c3ccc(cc3)c4ccccc4 2M A2 475.11 476.51 198 ClC(Cl)(Cl)c1nc(nc(n1)c2ccc(cc2)c3ccccc3)N4CCCNCC4 2M A7 447.08 448.15 199 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)c4ccccc4 2M A8 461.09 462.76 200 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)c4ccccc4 2M A10 461.09 462.27 201 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)c4ccccc4 2M A3 475.11 476.55 202 ClC1═CC(═CC(Cl)═C1)C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2L A1 452.98 454.60 203 Clc1cc(Cl)cc(c1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2L A2 467.00 468.05 204 ClC1═CC(═CC(Cl)═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCNCC1 2L A7 438.97 440.03 205 CN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC(Cl)═C1 2L A8 452.98 454.02 206 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cc(Cl)cc(Cl)c3 2L A12 452.98 454.07 207 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cc(Cl)cc(Cl)c3 2L A10 438.97 440.06 208 Clc1cc(Cl)cc(c1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2L A35 446.94 448.09 209 Clc1cc(Cl)cc(c1)c2nc(NCc3cccnc3)nc(n2)C(Cl)(Cl)Cl 2L A36 446.94 448.00 210 Clc1cc(Cl)cc(c1)c2nc(NCc3ccccn3)nc(n2)C(Cl)(Cl)Cl 2L A37 446.94 447.98 211 Clc1cc(Cl)cc(c1)c2nc(NCCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2L A38 460.95 462.03 212 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A12 453.05 213 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A10 439.03 440.08 214 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(F)(F)F 2F A11 427.03 428.14 215 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3OC 2V A17 429.09 430.12 216 COc1ccccc1c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2V A10 401.06 402.12 217 COc1ccccc1c2nc(NCC(C)(C)N)nc(n2)C(Cl)(Cl)Cl 2V A11 389.06 390.50 218 COc1ccccc1c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2V A7 401.06 402.53 219 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc4ccccc4c3 2J A10 421.06 422.17 220 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc3ccccc3c2 2J A4 437.09 438.22 221 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(C)cc3 2 A10 385.06 386.22 222 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A12 452.98 456.24 223 ClC(Cl)(Cl)c1nc(NCc2ccccn2)nc(n1)c3ccc4ccccc4c3 2J A37 429.03 430.62 224 ClC(Cl)(Cl)c1nc(NCCCN2CCCC2)nc(n1)c3ccc4ccccc4c3 2J A2 449.09 450.58 225 ClC(Cl)(Cl)c1nc(NCCc2ccccn2)nc(n1)c3ccc4ccccc4c3 2J A40 443.05 444.33 226 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc4ccccc4c3 2J A8 435.08 436.70 227 ClC(Cl)(Cl)c1nc(nc(n1)c2ccc3ccccc3c2)N4CCCNCC4 2J A7 421.06 422.21 228 ClC(Cl)(Cl)c1nc(NCCN2CCCC2)nc(n1)c3ccc4ccccc4c3 2J A1 435.08 436.63 229 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc4ccccc4c3 2J A3 449.09 450.65 230 ClC(Cl)(Cl)c1nc(NCCc2ccncc2)nc(n1)c3ccc4ccccc4c3 2J A38 443.05 444.87 231 ClC(Cl)(Cl)c1nc(NCCc2cccnc2)nc(n1)c3ccc4ccccc4c3 2J A39 443.05 444.55 232 ClC(Cl)(Cl)c1nc(NCc2cccnc2)nc(n1)c3ccc4ccccc4c3 2J A36 429.03 430.11 233 ClC(Cl)(Cl)c1nc(NCc2ccncc2)nc(n1)c3ccc4ccccc4c3 2J A35 429.03 430.64 234 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc4ccccc4c3 2J A12 435.08 436.20 235 ClC(Cl)(Cl)c1nc(Nc2ccncc2)nc(n1)c3ccc4ccccc4c3 2J A18 415.02 416.08 236 COc1cccc(c1)c2nc(NCCC3CCCN3C)nc(n2)C(Cl)(Cl)Cl 2A A3 429.08 430.22 237 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3 2I A12 385.06 386.12 238 COc1cccc(c1)c2nc(NCC(C)(C)N)nc(n2)C(Cl)(Cl)Cl 2A A11 389.06 390.12 239 CN1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3 2I A10 371.05 372.07 240 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccccc2 2I A4 387.08 388.15 241 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(OC)c3 2A A17 429.09 430.14 242 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(OC)c2 2A A4 417.09 418.18 243 CCN(CC)CCNc1nc(Cc2cccc(OC)c2)nc(n1)C(Cl)(Cl)Cl 2Y A4 431.10 432.12 244 Cc1ccc(cc1)c2nc(NCC(C)(C)N)nc(n2)C(Cl)(Cl)C1 2 A11 373.06 374.80 245 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(C)cc3 2 A12 399.08 400.18 246 CC(C)(C)c1ccc(cc1)c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2E A1 441.13 442.27 247 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C)CC1 2E A16 469.16 470.16 248 ClC(Cl)(Cl)c1nc(NCc2ccncc2)nc(n1)c3ccc(cc3)c4ccccc4 2M A35 455.05 456.57 249 ClC(Cl)(Cl)c1nc(NCc2cccnc2)nc(n1)c3ccc(cc3)c4ccccc4 2M A36 455.05 456.29 250 ClC(Cl)(Cl)c1nc(NCc2ccccn2)nc(n1)c3ccc(cc3)c4ccccc4 2M A37 455.05 456.11 251 ClC(Cl)(Cl)c1nc(NCCc2ccncc2)nc(n1)c3ccc(cc3)c4ccccc4 2M A38 469.06 470.12 252 ClC(Cl)(Cl)c1nc(NCCc2cccnc2)nc(n1)c3ccc(cc3)c4ccccc4 2M A39 469.06 470.38 253 ClC(Cl)(Cl)c1nc(NCCc2ccccn2)nc(n1)c3ccc(cc3)c4ccccc4 2M A40 469.06 470.62 254 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccccc2c3ccc(C)cc3 2O A4 477.13 478.18 255 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3c4ccc(C)cc4 2O A12 475.11 476.35 256 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3c4ccc(C)cc4 2O A17 489.13 491.06 257 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3)CC1 2C A16 481.02 482.13 258 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(OC)c3)CC1 2A A16 443.10 444.22 259 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccccc3c4ccc(C)cc4)CC1 2O A16 503.14 504.27 260 Cc1ccc(cc1)c2ccccc2c3nc(NCC(C)(C)N)nc(n3)C(Cl)(Cl)Cl 2O A11 449.09 450.55 261 CSc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCN(C)CC3 2G A8 431.05 432.05 262 CSc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2G A7 417.03 417.92 263 Cc1ccc(cc1)c2ccccc2c3nc(nc(n3)C(Cl)(Cl)Cl)N4CCCNCC4 2O A2 461.09 462.01 264 Cc1ccc(cc1)c2ccccc2c3nc(NCCCN4CCCC4)nc(n3)C(Cl)(Cl)Cl 2O A7 489.13 490.08 265 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(C)cc3)CC1 2 A16 427.11 428.06 266 Cc1ccc(cc1)c2ccccc2c3nc(NCCN4CCCC4)nc(n3)C(Cl)(Cl)Cl 2O A1 475.11 476.08 267 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(OC)cc3 2B A17 429.09 430.13 268 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(OC)cc2 2B A4 417.09 418.12 269 COc1cccc(Cc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCN(C)CC3)c1 2Y A8 429.09 270 CSc1ccc(cc1)c2nc(NC3CCN(C)CC3)nc(n2)C(Cl)(Cl)Cl 2G A12 431.05 431.98 271 COc1ccc(cc1)c2nc(NC(C)(C)CN)nc(n2)C(Cl)(Cl)Cl 2B A11 389.06 390.49 272 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3 2B A10 401.06 402.08 273 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(SC)cc3)CC1 2G A16 459.08 460.17 274 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(OC)cc3)CC1 2B A16 443.10 444.55 275 COc1ccc(cc1)c2nc(NC3CCN(C)CC3)nc(n2)C(Cl)(Cl)Cl 2B A12 415.07 416.16 276 CC(C)(C)c1ccc(ccpc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(CCO)CC3 2E A21 457.12 458.26 277 CSc1ccc(cc1)c2nc(NC(C)(C)CN)nc(n2)C(Cl)(Cl)Cl 2G A11 405.03 406.14 278 COc1ccc(c2nc(NCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl)c4ccccc14 2R A1 465.09 466.14 279 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(OC)c4ccccc34)CC1 2R A16 493.12 494.20 280 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(OC)c4ccccc34 2R A7 479.10 480.13 281 COc1ccc(c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3)c4ccccc14 2R A17 451.07 452.09 282 Clc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCNCC3 2D A7 405.01 406.02 283 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3)CC1 2D A16 447.06 448.12 284 CC(C)(N)CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)cc2 2D A11 393.01 394.05 285 CN1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A12 419.02 420.08 286 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cpcc2 2D A4 421.04 422.07 287 CN1CCCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A8 419.02 420.09 288 COc1cccc(Cc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCN(C)CC3)c1 2Y A10 415.07 416.38 289 COC1═CC═CC═C1CC1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCN(C)CC1 2W A8 429.09 430.32 290 COC1═CC═CC═C1CC1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCNCC1 2W A7 415.07 416.48 291 COC1═CC═CC═C1CC1═NC(NC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2W A12 429.09 430.22 292 COC1═CC═CC═C1CC1═NC(NCC(C)(C)N)═NC(═N1)C(Cl)(Cl)Cl 2W A11 403.07 404.25 293 CCN1CCC(CNC2═NC(CC3═CC═CC═C3OC)═NC(═N2)C(Cl)(Cl)Cl)CC1 2W A16 457.12 458.25 294 COC1═CC═CC═C1CC1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2W A1 429.09 430.39 295 CN1CCCC1CCNC1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A3 498.07 499.17 296 CC(C)(N)CNC1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A11 458.04 459.14 297 CCN1CCCC(Cl)NC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A17 475.11 476.16 298 CN1CCN(CC1)C1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A10 447.08 448.23 299 CC1═CC═C(C═C1)C1═C(C═CC═C1)C1═NC(NCC2═CC═NC═C2)═NC(═N1)C(Cl)(Cl)Cl 2O A35 469.06 471.17 300 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCC2═CC═NC-C2)-NC(═N1)C(Cl)(CDC1 2R A35 459.04 460.32 301 CCN1CCC(CNC2═NC(NC3═CC═C(OC(F)(F)F)C═C3)═NC(═N2)C(Cl)(Cl)Cl)CC1 1D A16 512.09 513.31 302 OCCN1CCN(CCl)C1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A21 500.05 501.02 303 NC1(CNC2═NC(NC3═CC═C(OC(F)(F)F)C═C3)═NC(═N2)C(Cl)(Cl)Cl)CCOCC1 1D A26 500.05 501.07 304 OCCN1CCN(CC1)C1═NC(═NC(═N1)C1═CC(Cl)═C(Cl)C═C1)C(Cl)(Cl)Cl 2C A23 468.98 472.23 305 OCCN1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C2C═CC═CC2═C1 2J A21 451.07 452.14 306 CCN1CCC(CNC2═NC(═NC(═N2)C(Cl)(Cl)Cl)C2═CC═C(C═C2)C2═CC═CC═C2)CC1 2M A16 489.13 490.25 307 CCN1CCC(CNC2═NC(═NC(═N2)C2═CC═C3C═CC═CC3═C2)C(Cl)(Cl)Cl)CC1 2J A16 463.11 464.25 308 OCCN1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)C1═CC═CC═C1 2M A21 477.09 478.67 309 CSC1═CC═C(C═C1)C1═NC(═NC(═N1)N1CCN(CCO)CC1)C(Cl)(Cl)Cl 2G A21 447.05 448.16 310 CCN1CCCC(Cl)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C2C═CC═CC2═C1 2J A17 449.09 450.19 311 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CCOCC1 2H A26 516.96 518.05 312 CC(C)(N)CNC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A11 359.05 360.13 313 NC1(CNC2═NC(═NC(═N2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CCOCC1 2I A26 401.06 402.13 314 CC(C)(C)C1═CC═C(C═C1)C1═NC(NCC2(N)CCOCC2)═NC(═N1)C(Cl)(Cl)Cl 2E A26 457.12 458.62 315 NC1(CNC2═NC(═NC(═N2)C2═CC(═CC═C2)C(F)(F)F)C(Cl)(Cl)Cl)CCOCC1 2F A26 469.05 470.15 316 CS(═O)(═O)C1═CC═C(C═C1)C1═NC(NCC2(N)CCOCC2)═NC(═N1)C(Cl)(Cl)Cl 6 A26 479.04 480.14 317 NC1(CNC2═NC(═NC(═N2)C2═CC3═C(C═CC═C3)C═C2)C(Cl)(Cl)Cl)CCOCC1 2J A26 451.07 452.26 318 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCC2(N)CCOCC2)═NC(═N1)C(Cl)(Cl)Cl 2R A26 481.08 482.37 319 COC1═C(OC)C═C(C═C1)C1═NC(NCC2(N)CCOCC2)═NC(═N1)C(Cl)(Cl)Cl 2S A26 461.08 462.35 320 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A31 427.11 428.22 321 CC(C)(C)C1═CC═C(C═C1)C1═NC(NC2CC(C)(C)NC(C)(C)C2)═NC(═N1)C(Cl)(Cl)Cl 2E A31 483.17 484.28 322 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC(═CC═C1)C(F)(F)F)C(Cl)(Cl)Cl 2F A31 495.10 496.17 323 CSC1═CC═C(C═C1)C1═NC(NC2CC(C)(C)NC(C)(C)C2)═NC(═N1)C(Cl)(Cl)Cl 2G A31 473.10 474.27 324 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═C(C═C1)S(C)(═O)═O)C(Cl)(Cl)Cl 6 A31 505.09 506.20 325 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═C(C═C1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl 2H A31 543.01 544.14 326 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC2═C(C═CC═C2)C═C1)C(Cl)(Cl)Cl 2J A31 477.13 478.26 327 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A31 503.14 504.27 328 COC1═C(OC)C═C(C═C1)C1═NC(NC2CC(C)(C)NC(C)(C)C2)═NC(═N1)C(Cl)(Cl)Cl 2S A31 487.13 488.22 329 CC(C)(N)CNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC2═C(C═CC═C2)C═C1 2J A11 409.06 410.13 330 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═C(Cl)C═C1)C(Cl)(Cl)Cl 2D A31 461.07 462.18 331 CC(C)(N)CNC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A11 435.08 436.23 332 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CCOCC1 2M A26 477.09 478.18 333 NC1(CNC2═NC(═NC(═N2)C2═CC═C(Cl)C═C2)C(Cl)(Cl)Cl)CCOCC1 2D A26 435.02 436.16 334 ClC1═CC═CC(═C1)C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2P A1 419.02 420.07 335 CN1CCCC1CCNC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A3 433.04 434.26 336 ClC1═CC═CC(═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCNCC1 2P A7 405.01 406.23 337 CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A12 419.02 420.36 338 CCN1CCCC(C1)NC1═NC(═NC(═N1)C1═CC(Cl)═CC═Cl)C(Cl)(Cl)Cl 2P A17 433.04 434.18 339 CCN1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC═C2)C(Cl)(Cl)Cl)CC1 2P A16 447.06 448.20 340 CSC1═CC═C(C═C1)C1═NC(NCC2(N)CCOCC2)═NC(═N1)C(Cl)(Cl)Cl 2G A26 447.05 448.17 341 COC1═CC═C(NC2═NC(NCCC3CCCN3C)═NC(═N2)C(Cl)(Cl)Cl)C═N1 1B A3 445.10 446.19 342 CCN(CC)CCNC1═NC(═NC(NC2═CC═C(OC)N═C2)═N1)C(Cl)(Cl)Cl 1B A4 433.10 434.17 343 COC1═CC═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCCNCC2)C═N1 1B A7 417.06 418.15 344 CCN1CCCC(C1)NC1═NC(═NC(NC2═CC═C(OC)N═C2)═N1)C(Cl)(Cl)Cl 1B A17 445.10 446.22 345 COC1═CC═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCN(C)CC2)C═N1 1B A10 417.06 418.13 346 COC1═C(NC2═NC(NCCC3CCCN3C)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A3 445.10 446.17 347 CCN(CC)CCNC1═NC(═NC(NC2═C(OC)N═CC═C2)═N1)C(Cl)(Cl)Cl 1A A4 433.10 434.19 348 COC1═C(NC2═NC(NC3CC(C)(C)NC(C)(C)C3)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A31 473.13 474.24 349 COC1═NC═C(NC2═NC(NC3CCN(C)CC3)═NC(═N2)C(Cl)(Cl)Cl)C═C1 1B A12 431.08 432.19 350 COC1═C(NC2═NC(NCCN3CCCC3)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A1 431.08 432.25 351 COC1═C(NC2═NC(NCCCN3CCCC3)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A2 445.10 446.27 352 CCN1CCC(CNC2═NC(═NC(NC3═C(OC)N═CC═C3)═N2)C(Cl)(Cl)Cl)CC1 1A A16 459.11 460.27 353 COC1═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCN(C)CC2)C═CC═N1 1A A10 417.06 418.20 354 COC1═C(NC2═NC(NC3CCN(C)CC3)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A12 431.08 432.17 355 CCN1CCCC(C1)NC1═NC(═NC(NC2═C(OC)N═CC═C2)═N1)C(Cl)(Cl)Cl 1A A17 445.10 446.21 356 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(Cl)C═C1)C(Cl)(Cl)Cl 2D A27 421.04 422.19 357 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC(═CC═C1)C(F)(F)F)C(Cl)(Cl)Cl 2F A27 455.07 456.23 358 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC(OC)═C(OC)C═Cl)C(Cl)(Cl)Cl 2S A27 447.10 448.25 359 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A27 405.07 406.54 360 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(SC)C═C1)C(Cl)(Cl)Cl 2G A27 433.07 434.58 361 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(C═C1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl 2H A27 502.98 504.19 362 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(C═C1)C(C)(C)C)C(Cl)(Cl)Cl 2E A27 443.14 444.34 363 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC(Cl)═CC(Cl)═C1)C(Cl)(Cl)Cl 2L A27 455.00 456.40 364 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A27 463.11 464.24 365 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(C═C1)S(C)(═O)═O)C(Cl)(Cl)Cl 6 A27 465.06 466.12 366 ClC(Cl)(Cl)C1═NC(NCCN2CCCC2)═NC(═N1)C1═CC═C(C═C1)N1CCCC1 2AA A1 454.12 455.23 367 COC1═CC═C(NC2═NC(NCCCN3CCCC3)═NC(═N2)C(Cl)(Cl)Cl)C═N1 1B A2 445.10 446.16 368 ClC(Cl)(Cl)C1═NC(NCCCN2CCCC2)═NC(═N1)C1═CC═C(C═C1)N1CCCC1 2AA A2 468.14 469.28 369 COC1═CC═C(NC2═NC(NCCN3CCCC3)═NC(═N2)C(Cl)(Cl)Cl)C═N1 1B A1 431.08 432.15 370 CN1CCCC1CCNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A3 468.14 469.28 371 CN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A8 454.12 455.22 372 CN1CCC(CC1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A12 454.12 455.26 373 CC(C)(N)CNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A11 428.10 429.22 374 CCN(CC)CCNC1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A4 486.07 487.18 375 CN1CCN(CC1)C1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A10 470.04 471.25 376 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A27 387.08 388.60 377 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC2═C(C═CC═C2)C═C1)C(Cl)(Cl)Cl 2J A27 437.09 438.35 378 COC1═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCCNCC2)C═CC═N1 1A A7 417.06 418.18 379 COC1═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCCN(C)CC2)C═CC═N1 1A A8 431.08 432.21 380 FC1═CC═C(C═C1)C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2Q A1 403.05 404.15 381 FC1═CC═C(C═C1)C1═NC(NCCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2Q A2 417.07 418.19 382 CN1CCCC1CCNC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A3 417.07 418.20 383 CCN(CC)CCNC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A4 405.07 406.21 384 CN1CCCN(CC1)C1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A8 403.05 404.25 385 CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A12 403.05 404.14 386 CCN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(F)C═C2)C(Cl)(Cl)Cl)CC1 2Q A16 431.08 432.28 387 CCN1CCCC(C1)NC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A17 417.07 418.21 388 CCC(N)(CC)CNC1═NC(═NC(═N1)C1═CC═C(Cl)C(Cl)═C1)C(Cl)(Cl)Cl 2C A27 455.00 456.16 389 CC(C)(N)CNC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A11 377.04 378.10 390 CN1CCN(CCl)C1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A10 389.04 390.15 391 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A31 445.10 446.21 392 COC1═C(OC)C═C(C═C1)C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2S A1 445.08 446.23 393 COC1═C(OC)C═C(C═C1)C1═NC(NCCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2S A2 459.10 460.23 394 COC1═C(OC)C═C(C═C1)C1═NC(NCCC2CCCN2C)═NC(═N1)C(Cl)(Cl)Cl 2S A3 459.10 460.23 395 CCN(CC)CCNC1═NC(═NC(═N1)C1═CC(OC)═C(OC)C═C1)C(Cl)(Cl)Cl 2S A11 447.10 448.25 396 COC1═C(OC)C═C(C═C1)C1═NC(NCC(C)(C)N)═NC(═N1)C(Cl)(Cl)Cl 2S A4 419.07 420.19 397 COC1═C(OC)C═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCNCC1 2S A7 431.07 432.19 398 COC1═C(OC)C═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCN(C)CC1 2S A8 445.08 446.20 399 COC1═C(OC)C═C(C═C1)C1═NC(NC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2S A12 445.08 446.28 400 COC1═C(OC)C═C(C═Cl)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(C)CC1 2S A10 431.07 432.22 401 CCN1CCC(CNC2═NC(═NC(═N2)C2═CC(OC)═C(OC)C═C2)C(Cl)(Cl)Cl)CC1 2S A16 473.12 474.27 402 CCN1CCCC(C1)NC1═NC(═NC(═N1)C1═CC(OC)═C(OC)C═C1)C(Cl)(Cl)Cl 2S A17 459.10 460.23 403 COC1═NC═C(NC2═NC(NCC(C)(C)N)═NC(═N2)C(Cl)(Cl)Cl)C═C1 1B A11 405.06 406.13 404 COC1═C(NC2═NC(NCC(C)(C)N)═NC(═N2)C(Cl)(Cl)Cl)C═CC═N1 1A A11 405.06 406.15 405 ClC(Cl)(Cl)C1═NC(═NC(NCCN2CCCC2)═N1)C1═CC═CC═C1 2I A1 385.06 386.21 406 ClC(Cl)(Cl)C1═NC(═NC(NCCCN2CCCC2)═N1)C1═CC═CC═C1 2I A2 399.08 400.27 407 CN1CCCC1CCNC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A3 399.08 400.29 408 ClC(Cl)(Cl)C1═NC(═NC(═N1)N1CCCNCC1)C1═CC═CC═C1 2I A7 371.05 372.16 409 CN1CCCN(CC1)C1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A8 385.06 386.19 410 CCN1CCC(CNC2═NC(═NC(═N2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2I A16 413.09 414.34 411 CCN(CC)CCNC1═NC(═NC(═N1)C1═C2C═CC═CC2═C(OC)C═C1)C(Cl)(Cl)Cl 2R A4 467.10 468.30 412 CCN(CC)CCNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A4 456.14 457.27 413 COC1═C2C═CC═CC2═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCCN(C)CC1 2R A7 465.09 466.55 414 COC1═C2C═CC═CC2═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(C)CC1 2R A8 451.07 452.22 415 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCC(C)(C)N)═NC(═N1)C(Cl)(Cl)Cl 2R A11 439.07 440.19 416 CC1═CC═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(CCO)CC1 2 A21 415.07 416.26 417 OCCN1CCN(CC1)C1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A21 401.06 402.18 418 OCCN1CCN(CC1)C1═NC(═NC(═N1)C1═CC(Cl)═CC(Cl)═C1)C(Cl)(Cl)Cl 2L A21 468.98 470.15 419 CC1═CC═C(C═C1)C1═CC═CC═C1C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(CCO)CC1 2O A21 491.10 492.28 420 OCCN1CCN(CC1)C1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A21 435.02 436.16 421 OCCN1CCN(CC1)C1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A21 419.05 420.15 422 COC1═C2C═CC═CC2═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(CCO)CC1 2R A21 481.08 482.65 423 COC1═C(OC)C═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCN(CCO)CC1 2S A21 461.08 462.19 424 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2R A2 479.10 480.63 425 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCCC2CCCN2C)═NC(═N1)C(Cl)(Cl)Cl 2R A3 479.10 480.23 426 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2R A12 465.09 466.34 427 CN1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A10 440.10 441.33 428 ClC(Cl)(Cl)C1═NC(═NC(═N1)C1═CC═C(C═C1)N1CCCC1)N1CCCNCC1 2AA A7 440.10 441.33 429 CCN1CCCC(C1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A17 468.14 469.28 430 CCN1CCC(CNC2═NC(═NC(═N2)C(Cl)(Cl)Cl)C2═CC═C(C═C2)N2CCCC2)CC1 2AA A16 482.15 483.33 431 OCCN1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A21 470.12 471.33 432 NC1(CNC2═NC(═NC(═N2)C(Cl)(Cl)Cl)C2═CC═C(C═C2)N2CCCC2)CCOCC1 2AA A26 470.12 471.22 433 ClC1═CC═CC(═C1)C1═NC(NCCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2P A2 433.04 434.16 434 CCN(CC)CCNC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A4 421.04 422.17 435 CN1CCCN(CC1)C1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A8 419.02 420.15 436 CN1CCN(CC1)C1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A10 405.01 406.15 437 CC(C)(N)CNC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A11 393.01 394.09 438 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A31 461.07 462.34 439 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═C(C)C═C1)C(Cl)(Cl)Cl 2 A24 387.08 388.58 440 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═C(C═C1)C(C)(C)C)C(Cl)(Cl)Cl 2E A24 429.13 430.25 441 CSC1═CC═C(C═C1)C1═NC(NCCCN(C)C)═NC(═N1)C(Cl)(Cl)Cl 2G A24 419.05 420.21 442 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═C(C═C1)S(C)(═O)═O)C(Cl)(Cl)Cl 6 A24 451.04 452.39 443 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I A24 373.06 374.24 444 CN(C)CCCNC1═NC(═NC(═N1)C1═CC2═C(C═CC═C2)C═C1)C(Cl)(Cl)Cl 2J A24 423.08 424.21 445 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M A24 449.09 450.01 446 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═CC═C1C1═CC═C(C)C═C1)C(Cl)(Cl)Cl 2O A24 463.11 464.65 447 CN(C)CCCNC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P A24 407.02 408.18 448 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═C(F)C═C1)C(Cl)(Cl)Cl 2Q A24 391.05 392.33 449 COC1═CC═C(C2═NC(NCCCN(C)C)═NC(═N2)C(Cl)(Cl)Cl)C2═C1C═CC═C2 2R A24 453.09 454.29 450 COC1═CC═C(C═C1OC)C1═NC(NCCCN(C)C)═NC(═N1)C(Cl)(Cl)Cl 2S A24 433.08 434.37 451 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)C1═CC═CC═C1 2M A23 491.10 492.22 452 [O−][N+](═O)C1═CC═CC═C1C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2N A1 430.05 431.52 453 CC1═CC═C(C═C1)C1═NC(═NC(═N1)N1CCCN(CCO)CC1)C(Cl)(Cl)Cl 2 A23 429.09 430.27 454 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═C(Cl)C═C1 2C A23 483.00 484.17 455 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C═C1 2D A23 449.03 450.17 456 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(═CC═C1)C(F)(F)F 2G A23 483.06 484.20 457 CSC1═CC═C(C═C1)C1═NC(═NC(═N1)N1CCCN(CCO)CC1)C(Cl)(Cl)Cl 6 A23 461.06 462.26 458 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═CC═C1 2I A23 415.07 416.18 459 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC2═C(C═CC═C2)C═C1 2J A23 465.09 466.20 460 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC(Cl)═C1 2L A23 483.00 484.16 461 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC═C1 2P A23 449.03 450.13 462 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(F)C═C1 2Q A23 433.06 434.17 463 COC1═C2C═CC═CC2═C(C═C1)C1═NC(═NC(═N1)N1CCCN(CCO)CC1)C(Cl)(Cl)Cl 2R A23 495.10 496.20 464 COC1═C(OC)C═C(C═C1)C1═NC(═NC(═N1)N1CCCN(CCO)CC1)C(Cl)(Cl)Cl 2S A23 475.09 476.30 465 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)N1CCCC1 2AA A23 484.13 485.35 466 CCN1CCCC(C1)NC1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A17 444.06 445.23 467 CC(C)(N)CNC1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A11 404.03 407.28 468 OCCN1CCCN(CC1)C1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A23 514.07 515.34 469 ClC1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2D A5 427.99 429.11 470 ClC1═CC═C(C═C1Cl)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2C A5 461.95 463.09 471 ClC1═CC(═CC(Cl)═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2L A5 461.95 463.16 472 ClC1═CC(═CC═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2P A5 427.99 429.14 473 CN(CCC1═NC═CC═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C═C1 2D A19 441.01 442.14 474 CN(CCC1═NC═CC═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC(Cl)═C1 2L A19 474.97 476.14 475 CN(CCC1═NC═CC═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═CC(Cl)═C1 2P A19 441.01 442.18 476 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCCN2CCCC2)═N1)C(Cl)(Cl)Cl 2T A1 445.08 446.29 477 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCCCN2CCCC2)═N1)C(Cl)(Cl)Cl 2T A2 459.10 460.25 478 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCCC2CCCN2C)═N1)C(Cl)(Cl)Cl 2T A3 459.10 460.27 479 CCN(CC)CCNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(OC)═CC(OC)═C1 2T A4 447.10 448.21 480 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)N1CCCN(C)CC1)C(Cl)(Cl)Cl 2T A8 445.08 446.19 481 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCC(C)(C)N)═N1)C(Cl)(Cl)Cl 2T A11 419.07 420.17 482 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)N1CCN(C)CC1)C(Cl)(Cl)Cl 2T A10 431.07 432.21 483 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)N1CCCN(CCO)CC1)C(Cl)(Cl)Cl 2T A23 475.09 476.22 484 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C)C═C2)C(Cl)(Cl)Cl)CC1 2 A32 441.12 442.28 485 COC1═CC═CC(═C1)C1═NC(NCC2CCN(CC2)C(C)C)═NC(═N1)C(Cl)(Cl)Cl 2A A32 457.12 458.27 486 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═C(Cl)C═C2)C(Cl)(Cl)Cl)CC1 2C A32 495.03 496.31 487 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(Cl)C═C2)C(Cl)(Cl)Cl)CC1 2D A32 461.07 462.22 488 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(C)(C)C)C(Cl)(Cl)Cl)CC1 2E A32 483.17 484.36 489 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC(═CC═C2)C(F)(F)F)C(Cl)(Cl)Cl)CC1 2F A32 495.10 496.32 490 CSC1═CC═C(C═C1)C1═NC(NCC2CCN(CC2)C(C)C)═NC(═N1)C(Cl)(Cl)Cl 2G A32 473.10 474.27 491 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)S(C)(═O)═O)C(Cl)(Cl)Cl)CC1 6 A32 505.09 506.25 492 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CC1 2H A32 543.01 544.12 493 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2I A32 427.11 428.44 494 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC3═C(C═CC═C3)C═C2)C(Cl)(Cl)Cl)CC1 2J A32 479.14 478.24 495 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC(Cl)═C2)C(Cl)(Cl)Cl)CC1 2L A32 495.03 496.23 496 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2M A32 503.14 504.34 497 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═C(C═CC═C2)[N+]([O−])═O)C(Cl)(Cl)Cl)CC1 2N A32 472.09 473.18 498 COC1═CC═C(C2═NC(NCC3CCN(CC3)C(C)C)═NC(═N2)C(Cl)(Cl)Cl)C2═C1C═CC═C2 2R A32 507.14 508.29 499 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC═C2)C(Cl)(Cl)Cl)CC1 2P A32 461.07 462.21 500 CC(C)N1CCC(CNC2═NC(═NC(═N2)C2═CC═C(F)C═C2)C(Cl)(Cl)Cl)CC1 2Q A32 445.10 446.25 501 COC1═C(OC)C═C(C═C1)C1═NC(NCC2CCN(CC2)C(C)C)═NC(═N1)C(Cl)(Cl)Cl 2S A32 487.13 488.36 502 COC1═CC(═CC(OC)═C1)C1═NC(NCC2CCN(CC2)C(C)C)═NC(═N1)C(Cl)(Cl)Cl 2T A32 487.13 488.27 503 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C)C═C2)C(Cl)(Cl)Cl)CC1 2 A33 413.09 414.34 504 COC1═CC═CC(═C1)C1═NC(NCC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2A A33 429.09 430.26 505 CN1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═C(Cl)C═C2)C(Cl)(Cl)Cl)CC1 2C A33 467.00 468.17 506 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(Cl)C═C2)C(Cl)(Cl)Cl)CC1 2D A33 433.04 434.22 507 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(C)(C)C)C(Cl)(Cl)Cl)CC1 2E A33 455.14 456.31 508 CN1CCC(CNC2═NC(═NC(═N2)C2═CC(═CC═C2)C(F)(F)F)C(Cl)(Cl)Cl)CC1 2F A33 467.07 468.46 509 CSC1═CC═C(C═C1)C1═NC(NCC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2G A33 445.07 446.37 510 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)S(C)(═O)═O)C(Cl)(Cl)Cl)CC1 6 A33 477.06 478.18 511 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CC1 2H A33 514.98 516.08 512 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2I A33 399.08 400.49 513 CN1CCC(CNC2═NC(═NC(═N2)C2═CC3═C(C═CC═C3)C═C2)C(Cl)(Cl)Cl)CC1 2J A33 449.09 450.25 514 CN1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC(Cl)═C2)C(Cl)(Cl)Cl)CC1 2L A33 467.00 468.25 515 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2M A33 475.11 476.28 516 CN1CCC(CNC2═NC(═NC(═N2)C2═C(C═CC═C2)[N+]([O−])═O)C(Cl)(Cl)Cl)CC1 2N A33 444.06 445.19 517 COC1═CC═C(C2═NC(NCC3CCN(C)CC3)═NC(═N2)C(Cl)(Cl)Cl)C2═C1C═CC═C2 2R A33 479.10 480.29 518 CN1CCC(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC═C2)C(Cl)(Cl)Cl)CC1 2P A33 433.04 434.19 519 CN1CCC(CNC2═NC(═NC(═N2)C2═CC═C(F)C═C2)C(Cl)(Cl)Cl)CC1 2Q A33 417.07 418.21 520 COC1═C(OC)C═C(C═C1)C1═NC(NCC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2S A33 459.10 460.24 521 COC1═CC(═CC(OC)═C1)C1═NC(NCC2CCN(C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2T A33 459.10 460.25 522 [O−][N+](═O)C1═C(C═CC═C1)C1═NC(NCCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2N A2 444.06 445.21 523 CCN(CC)CCNC1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A4 432.06 433.18 524 CN1CCCC1CCNC1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A3 444.06 445.22 525 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)N1CCCNCC1)C(Cl)(Cl)Cl 2T A7 431.07 432.16 526 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)N1CCN(CCO)CC1)C(Cl)(Cl)Cl 2T A21 461.08 462.18 527 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NC2CC(C)(C)NC(C)(C)C2)═N1)C(Cl)(Cl)Cl 2T A31 487.13 488.25 528 CCN1CCCC(C1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(OC)═CC(OC)═C1 2T A17 459.10 460.27 529 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCC2(N)CCOCC2)═N1)C(Cl)(Cl)Cl 2T A26 461.08 462.19 530 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCC2(N)CCCC2)═N1)C(Cl)(Cl)Cl 2T A28 445.08 446.72 531 COC1═CC(═CC(OC)═C1)C1═NC(NCCCN(C)C)═NC(═N1)C(Cl)(Cl)Cl 2T A24 433.08 434.19 532 CN(C)CCCNC1═NC(═NC(═N1)C1═CC═CC═C1[N+]([O−])═O)C(Cl)(Cl)Cl 2N A24 418.05 419.10 533 COC1═CC(═CC═C1)C1═NC(NCCCN(C)C)═NC(═N1)C(Cl)(Cl)Cl 2 A24 403.07 404.16 534 CN(CCC1═NC═CC═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)C(Cl)(Cl)Cl 2H A19 522.95 524.08 535 CC1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2 A5 408.04 409.18 536 COC1═CC(═CC═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2A A5 424.04 425.17 537 COC1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2B A5 424.04 425.38 538 CC(C)(C)C1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2E A5 450.09 451.20 539 FC(F)(F)C1═CC(═CC═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2F A5 462.01 463.24 540 ClC(Cl)(Cl)C1═NC(NCCC2═CN═CC═N2)═NC(═N1)C1═CC═CC═C1 2I A5 394.03 395.18 541 ClC(Cl)(Cl)C1═NC(NCCC2═CN═CC═N2)═NC(═N1)C1═CC═C2C═CC═CC2═C1 2J A5 444.04 445.19 542 ClC(Cl)(Cl)C1═NC(NCCC2═CN═CC═N2)═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1 2M A5 470.06 471.18 543 CSC1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2G A5 440.01 441.13 544 [O−][N+](═O)C1═CC═CC═C1C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2N A5 439.01 440.21 545 CC1(C)OC2═C(C═C1)C═C(C═C2)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2U A5 476.07 477.25 546 COC1═CC═C(C2═C1C═CC═C2)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2R A5 474.05 475.16 547 FC1═CC═C(C═C1)C1═NC(═NC(NCCC2═CN═CC═N2)═N1)C(Cl)(Cl)Cl 2Q A5 412.07 413.16 548 CN1CCCN(CC1)C1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A8 430.05 431.24 549 CN1CCN(CC1)C1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A10 416.03 417.21 550 CN1CCC(CC1)NC1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A12 430.05 431.16 551 CCN1CCC(CNC2═NC(═NC(═N2)C2═C(C═CC═C2)[N+]([O−])═O)C(Cl)(Cl)Cl)CC1 2N A16 458.08 459.23 552 OCCN1CCCN(CC1)C1═NC(═NC(═N1)C1═C(C═CC═C1)[N+]([O−])═O)C(Cl)(Cl)Cl 2N A23 460.06 461.20 553 CC1(C)OC2═C(C═C1)C═C(C═C2)C1═NC(NCCN2CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2U A1 467.10 468.90 554 CC1(C)CC(CC(C)(C)N1)NC1═NC(═NC(═N1)C1═CC(Cl)═C(Cl)C═Cl)C(Cl)(Cl)Cl 2C A31 495.03 496.36 555 CC(C)(N)CNC1═NC(═NC(NC2═CC(═CC═C2)C(F)(F)F)═N1)C(Cl)(Cl)Cl 1I A11 442.05 443.31 556 CC(C)(N)CNC1═NC(═NC(NC2═CC(Cl)═CC(Cl)═C2)═N1)C(Cl)(Cl)Cl 1F A11 441.98 443.60 557 CC(C)(N)CNC1═NC(NC2═CC═CC═C2)═NC(═N1)C(Cl)(Cl)Cl 1G A11 374.06 375.65 558 Clc1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2D A2 94-97 559 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)cc3 2D A17 132-135 560 ClC(Cl)(Cl)c1nc(NCCCCCN2CCCC2)nc(n1)C(Cl)(Cl)Cl 2D A24 129-131 561 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)cc2 2D A62 103-106 562 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(F)(F)F 2F A24 97-99 563 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(F)(F)F 2AC A24  98-100 564 FC(F)(F)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AC A3 92-94 565 CN(CCCNC1═NC(C2═CC═C(C(Cl)(Cl)Cl)C═C2)═NC(C(Cl)(Cl)Cl)═N1)C 2H A24 120-123 566 CN(CCCNC1═NC(C2═CC═CC(C(Cl)(Cl)Cl)═C2)═NC(C(Cl)(Cl)Cl)═N1)C 2AD A24 107-109 567 CCN(CC)CCNC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═CC(═C1)C(Cl)(Cl)Cl 2AD A4 89-92 568 CCN(CCNC1═NC(C2═CC═C(C(Cl)(Cl)Cl)C═C2)═NC(C(Cl)(Cl)Cl)═N1)CC 2H A4 84-87 569 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A17 134-136 570 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2H A2 215-218 571 ClC(Cl)(Cl)c1cccc(c1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AD A2 102-105 572 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(F)(F)F 2F A4 158-160 573 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(cc(c2)C(F)(F)F)C(F)(F)F 2AE A24 113-115 574 FC(F)(F)c1cccc(c1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2F A2 80-82 575 FC(F)(F)c1cc(cc(c1)C(F)(F)F)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AE A2 125-127 576 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(cc(c2)C(F)(F)F)C(F)(F)F 2AE A4 86-89 577 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A17 151-153 578 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(F)(F)F 2F A17 126-128 579 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(F)(F)F 2AC A17 139-140 580 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cc(cc(c3)C(F)(F)F)C(F)(F)F 2AE A17 102-104 581 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A4 107-108 582 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(F)(F)F 2AC A4 90-92 583 Clc1ccc(cc1Cl)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2C A2 138-139 584 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(cc(c2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl 2AF A24 141-143 585 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A3  98-101 586 CC(CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(Cl)(Cl)Cl)N(C)C 2H A54 138-140 587 CCN(CC)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(Cl)(Cl)Cl 2AD A63 152.5-157.5 588 ClC(Cl)(Cl)c1cc(cc(c1)C(Cl)(Cl)Cl)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 2AF A2 132-135 589 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(Cl)(Cl)Cl 2AD A3 134-136 590 CC(CN(C)C)Nc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(Cl)(Cl)Cl 2AD A55 93-96 591 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(Cl)(Cl)Cl)C1 2AD A64 104-107 592 CN1CCCCC1CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(Cl)(Cl)Cl 2AD A65 109-112 593 CC(CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(Cl)(Cl)Cl)N(C)C 2AD A54 115-117 594 CCOC(═O)c1ccc(cc1)c2nc(NCC3CCN(CC)C3)nc(n2)C(Cl)(Cl)Cl 2AB A64 147-150 595 CCOC(═O)c1ccc(cc1)c2nc(NCC3CCCCN3C)nc(n2)C(Cl)(Cl)Cl 2AB A65 105-108 596 CCN1CCC(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl)C1 2H A64 136-140 597 CN(C)C1CCC(CC1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A66 528.99 598 CCOC(═O)c1ccc(cc1)c2nc(NCCCN(C)C)nc(n2)C(Cl)(Cl)Cl 2AB A24 110-112 599 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2•ClC(Cl)(Cl)ciccc(cc1)C(Cl)(Cl)Cl 2C A4 600 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(F)(F)F•ClC(Cl)(Cl)c1ccc(cc1)C(Cl)(Cl)Cl 2AC A4 601 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)C(Cl)(Cl)ClClC(Cl)(Cl)c1ccc(cc1)C(Cl)(Cl)Cl 2H A4 602 FC(F)(F)c1cccc(c1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)ClClC(Cl)(Cl)c1ccc(cc1)C(Cl)(Cl)Cl 2F A2 603 CCN(CC)CCC(C)Nc1nc(nc(n1)C(Cl)(Cl)Cl)c2cccc(c2)C(Cl)(Cl)Cl 2AD A67 115-120 604 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)C(Cl)(Cl)ClClC(Cl)(Cl)c1ccc(cc1)C(Cl)(Cl)Cl 1I A24 605 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A3 117-120 606 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A24 124.5-128   607 FC(F)(F)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl•ClC(Cl)(Cl)c1ccc(cc1)C(Cl)(Cl)Cl 2AC A2 608 CN1CCCCC1CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A65 165.5-169   609 CN1CCCC1CCNc2nc(nc(n2)C(Cl)(Cl)Cl)c3cc(Cl)cc(Cl)c3 2L A3 111-113 610 CC(CN(C)C)Nc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(Cl)cc(Cl)c2 2L A55 131-133 611 CN(C)CCCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(Cl)cc(Cl)c2 2L A24 207-212 612 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2cc(Cl)cc(Cl)c2 2L A4 233-234 613 CCN1CCC(CC1)C(C)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3 2C A22 136-139 614 CCN1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cc(Cl)cc(Cl)c3 2L A17 195.5-198.5 615 CCN(CC)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)S(═O)C 5 A4 449.06 450.11 616 CS(═O)c1ccc(cc1)c2nc(NCCCN3CCCC3)nc(n2)C(Cl)(Cl)Cl 5 A2 461.06 462.28 617 CCN(CC)C1CCCC(C1)Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3cccc(c3)C(Cl)(Cl)Cl 2AD A71 145-150 618 CN(C)CCNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)c(Cl)c2 2C A63 124.5-128   619 CCCN(CCC)CC(C)Nc1nc(Nc2cc(Cl)cc(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1F A72 108.5-112.5

TABLE 6 MS, MS, found Cmpd SMILES Preparation calc'd (M + 1) 620 COC1═CC═C(C2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CCC(N)CC2)C2═C1C═CC═C2 2R 451.07 452.56 621 NC1CCN(CC1)C1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I 371.08 372.43 622 NC1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C(Cl)═C1 2C 438.97 440.08 623 CC1═CC═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 2 385.06 386.25 624 CC(C)(C)C1═CC═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 2E 427.11 428.32 625 NC1CCN(CC1)C1═NC(═NC(═N1)C1═CC═CC(═C1)C(F)(F)F)C(Cl)(Cl)Cl 2F 439.03 440.15 626 CSC1═CC═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 2G 417.03 418.15 627 CS(═O)(═O)C1═CC═C(C═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 6 449.02 450.09 628 NC1CCN(CC1)C1═NC(═NC(═N1)C1═CC2═C(C═CC═C2)C═C1)C(Cl)(Cl)Cl 2J 421.05 422.19 629 COC1═CC(═CC═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 2A 401.06 402.20 630 NC1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C═C1 2D 405.01 407.00 631 NC1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC(Cl)═C1 2L 438.97 440.07 632 NC1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═C(C═CC═C1)[N+]([O−])═O 2N 416.03 417.17 633 NC1CCN(CC1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC(Cl)═CC═C1 2P 405.01 406.13 634 NC1CCN(CC1)C1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M 447.08 448.34 635 COC1═CC(═CC(OC)═C1)C1═NC(═NC(═N1)C(Cl)(Cl)Cl)N1CCC(N)CC1 2T 431.07 432.57

TABLE 7 MS, MS, found (M + 1) Cmpd SMILES Prep. Amine calc'd or mp (° C.) 636 CN(C)CCCNc1nc(Nc2ccc(Cl)cc2)nc(n1)C(Cl)(Cl)Cl 7 A24 226-228 637 CN(C)CCCNc1nc(Nc2ccc(Cl)c(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1F A24 215-217 638 CCN1CCCC(C1)Nc2nc(Nc3cc(Cl)cc(Cl)c3)nc(n2)C(Cl)(Cl)Cl 1F A17 198-202 639 CC(CN(C)C)Nc1nc(Nc2cc(Cl)cc(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1F A55 168-172 640 CC(CN(C)C)Nc1nc(Nc2ccc(Cl)c(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1C A55   153-155.5 641 CC(CNc1nc(Nc2ccc(Cl)c(Cl)c2)nc(n1)C(Cl)(Cl)Cl)N(C)C 1C A54   255-255.5 642 CCN(CC)CC(C)Nc1nc(Nc2ccc(Cl)c(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1C A68   180-183.5 643 CCN1CCC(CC1)C(C)Nc2nc(Nc3ccc(Cl)c(Cl)c3)nc(n2)C(Cl)(Cl)Cl 1C A22 105-109 644 CCN(CC)CC(C)Nc1nc(Nc2cc(Cl)cc(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1F A68 218-220 645 CCN1CCC(CC1)C(C)Nc2nc(Nc3cc(Cl)cc(Cl)c3)nc(n2)C(Cl)(Cl)Cl 1F A22 235-238 646 CCN(CC)CCCC(C)Nc1nc(Nc2ccc(Cl)c(Cl)c2)nc(n1)C(Cl)(Cl)Cl 1C A69  98-102 647 ClC(C1═NC(NCCO)═NC(C2═CC(C(F)(F)F)═CC═C2)═N1)(Cl)Cl 2F A57 399.99 401.06 648 CN1CCN(CC1)c2ccc(Nc3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)S(═O)(═O)C)cc2 6 A43 540.67 541.38 649 CC(C)(CNc1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(cc2)S(═O)(═O)C)CN3CCCCCC3 6 A48 533.12 534.04 650 CS(═O)(═O)c1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 6 A35 456.99 458.34 651 COc1ncccc1Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C 6 A13 472.99 473.94 652 ClC(Cl)(Cl)c1ccc(cc1)c2nc(NCc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2H A35 494.91 496.02 653 CN(Cc1ccccc1c2cccnc2)c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)C(Cl)(Cl)Cl 2H A49 570.95 654 CS(═O)(═O)c1ccc(cc1)c2nc(Nc3cccnc3)nc(n2)C(Cl)(Cl)Cl 6 A50 442.98 444.01 655 CCN1CCCC(C1)NC1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A17 498.07 499.12 656 FC(F)(F)OC1═CC═C(NC2═NC(═NC(NCCN3CCCC3)═N2)C(Cl)(Cl)Cl)C═C1 1D A1 484.06 485.14 657 FC(F)(F)OC1═CC═C(NC2═NC(═NC(NCCCN3CCCC3)═N2)C(Cl)(Cl)Cl)C═C1 1D A2 498.07 499.10 658 CN1CCCN(CC1)C1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A8 484.06 485.07 659 FC(F)(F)OC1═CC═C(NC2═NC(═NC(═N2)N2CCCNCC2)C(Cl)(Cl)Cl)C═C1 1D A7 470.04 471.07 660 CC1═CC═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2 A28 413.09 414.16 661 COC1═CC═CC(═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2A A28 429.09 430.12 662 CC(C)(C)C1═CC═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2E A28 455.14 456.22 663 NC1(CNC2═NC(═NC(═N2)C2═CC(═CC═C2)C(F)(F)F)C(Cl)(Cl)Cl)CCCCC1 2F A28 467.07 468.14 664 CSC1═CC═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2G A28 445.07 446.11 665 CS(═O)(═O)C1═CC═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 6 A28 477.06 478.16 666 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CCCCC1 2H A28 514.98 516.03 667 NC1(CNC2═NC(═NC(═N2)C2═CC3═C(C═CC═C3)C═C2)C(Cl)(Cl)Cl)CCCCC1 2J A28 449.09 450.17 668 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2R A28 479.10 480.23 669 COC1═C(OC)C═C(C═C1)C1═NC(NCC2(N)CCCCC2)═NC(═N1)C(Cl)(Cl)Cl 2S A28 459.10 460.78 670 NC1(CNC2═NC(═NC(═N2)C2═CC(Cl)═C(Cl)C═C2)C(Cl)(Cl)Cl)CCCCC1 2C A28 467.00 468.03 671 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CCCC1 2H A29 500.96 501.94 672 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CCCC1 2M A29 435.08 436.12 673 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NCC2(N)CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2R A29 465.09 466.18 674 COC1═C(OC)C═C(C═C1)C1═NC(NCC2(N)CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2S A29 445.08 446.17 675 COC1═CC═CC(═C1)C1═NC(NCC2(N)CCCC2)═NC(═N1)C(Cl)(Cl)Cl 2A A29 415.07 416.15 676 CN1CCC(CC1)NC1═NC(NC2═CC═C(OC(F)(F)F)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1D A12 484.06 484.91 677 NC1(CNC2═NC(═NC(═N2)C2═CC═CC═C2)C(Cl)(Cl)Cl)CC1 2I A30 357.03 358.14 678 NC1(CNC2═NC(═NC(═N2)C2═CC═C(Cl)C═C2)C(Cl)(Cl)Cl)CC1 2D A30 390.99 392.10 679 NC1(CNC2═NC(═NC(═N2)C2═CC═C(C═C2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)CC1 2H A30 472.93 474.08 680 NC1(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC═C2)C(Cl)(Cl)Cl)CC1 2P A30 390.99 392.12 681 CC1═CC═C(C═C1)C1═NC(NCC2(N)CC2)═NC(═N1)C(Cl)(Cl)Cl 2 A30 371.05 372.09 682 NC1(CNC2═NC(═NC(═N2)C2═CC(═CC═C2)C(F)(F)F)C(Cl)(Cl)Cl)CC1 2F A30 425.02 426.57 683 NC1(CNC2═NC(═NC(═N2)C2═CC(Cl)═CC(Cl)═C2)C(Cl)(Cl)Cl)CC1 2L A30 424.95 426.08 684 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═C(C═CC═C1)[N+]([O−])═O 2N A25 472.09 473.27 685 COC1═CC(═CC(OC)═C1)C1═NC(═NC(NCC2(N)CCCCC2)═N1)C(Cl)(Cl)Cl 2T A28 459.10 460.19 686 ClC(Cl)(Cl)C1═NC(NCCN2CCCC2)═NC(NC2═CC3═C(C═CC═C3)C═C2)═N1 1H A1 450.09 451.31 687 CN(CC(═O)OC(C)(C)C)c1nc(nc(n1)C(Cl)(Cl)Cl)c2ccc(Cl)cc2 2D A61 450.02 451.29 688 NC(═O)C1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H A53 514.94 516.08 689 CS(═O)(═O)c1ccc(cc1)c2nc(Nc3ccc(cc3)n4cccn4)nc(n2)C(Cl)(Cl)Cl 6 A42 508.00 510.95 690 CS(═O)(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCC(CC3)C(═O)N 6 A53 477.02 478.21 691 CC(═O)Nc1cccc(Nc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)S(═O)(═O)C)c1 6 A44 499.00

TABLE 8 MS, Cmpd SMILES Prep. MS, calc'd found (M + 1) 692 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C(Cl)═C1 2C 495.03 496.17 693 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(Cl)C═C1 2D 461.07 462.21 694 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C(Cl)(Cl)Cl)C1═CC═C(C═C1)C(C)(C)C 2E 483.17 484.47 695 CSC1═CC═C(C═C1)C1═NC(═NC(NC2CCN(CC(C)C)CC2)═N1)C(Cl)(Cl)Cl 2G 473.10 474.22 696 COC1═CC═C(C═C1)C1═NC(NC2CCN(CC(C)C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2B 457.12 458.23 697 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC═C(C═C1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl 2H 543.01 544.13 698 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC2═C(C═CC═C2)C═C1)C(Cl)(Cl)Cl 2J 477.13 478.32 699 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC═C(C═C1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2M 503.14 504.29 700 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC(═CC═C1)C(F)(F)F)C(Cl)(Cl)Cl 2F 495.10 496.26 701 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC(Cl)═CC═C1)C(Cl)(Cl)Cl 2P 461.07 462.18 702 COC1═C(OC)C═C(C═C1)C1═NC(NC2CCN(CC(C)C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2S 487.13 488.29 703 COC1═C2C═CC═CC2═C(C═C1)C1═NC(NC2CCN(CC(C)C)CC2)═NC(═N1)C(Cl)(Cl)Cl 2R 507.14 508.25 704 CC(C)CN1CCC(CC1)NC1═NC(═NC(═N1)C1═CC═CC═C1)C(Cl)(Cl)Cl 2I 427.11 428.30

TABLE 9 MS, found Cmpd SMILES Prep. Amine MS, calc'd (M + 1) 705 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(Cl)c(Cl)c4 2C A6 537.01 706 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4C(═O)OC(C)(C)C 2B A6 499.09 707 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4cccc(c4)C(F)(F)F 2F A6 537.07 708 Cc1cc(CNc2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(Cl)c(Cl)c3)n(C)n1 2C A46 463.96 709 Clc1ccc(Nc2nc(nc(n2)C(Cl)(Cl)Cl)N3CCOCC3)cc1C1 1 A51 440.95 442.12 710 CSc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4C(═O)OC(C)(C)C 2G A6 515.07 515.87 711 Cc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4C(═O)OC(C)(C)C 2B A6 483.10 484.01 712 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)C(C)(C)C 2E A6 525.15 525.99 713 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)C(Cl)(Cl)Cl 2H A6 584.98 586.14 714 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccccc4 2I A6 469.08 469.96 715 CC(C)(C)OC(═O)N1CC2CC1CN2c3nc(nc(n3)C(Cl)(Cl)Cl)c4ccc(cc4)S(═O)(═O)C 6 A6 547.06 548.11

TABLE 10 MS, Cmpd SMILES Prep. MS, calc'd found (M + 1) 716 Clc1ccc(cc1Cl)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2C 436.95 717 Clc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2D 402.99 718 COc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2B 399.04 400.25 719 Cc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2 383.05 384.03 720 ClC(Cl)(Cl)c1nc(nc(n1)c2ccccc2)N3CC4CC3CN4 2I 369.03 370.01 721 CC(C)(C)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2E 425.09 426.30 722 ClC(Cl)(Cl)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2H 484.93 486.08 723 CSc1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 2G 415.02 416.02 724 CS(═O)(═O)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CC4CC3CN4 6 447.01 448.00 725 FC(F)(F)OC1═CC═C(NC2═NC(═NC(═N2)C(Cl)(Cl)Cl)N2CC3CC2CN3)C═C1 1D 468.02 469.20 726 ClC(Cl)(Cl)C1═NC(═NC(═N1)C1═CC═C(C═C1)N1CCCC1)N1CC2CC1CN2 2AA 438.09 439.30

TABLE 11 MS, MS, found Cmpd SMILES Prep. Amine calc'd (M + 1) 727 CC(═O)Nc1cccc(Nc2nc(nc(n2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)c1 2Z A44 460.89 461.99 728 ClC(Cl)(Cl)c1nc(NCCCN2CCCC2)nc(Nc3ccc(cc3)n4cccn4)n1 7C A2 480.11 481.20 729 ClC(Cl)(Cl)c1nc(Nc2ccccc2N3CCOCC3)nc(n1)C(Cl)(Cl)Cl 2Z A41 488.93 490.08 730 COc1ccccc1Nc2nc(nc(n2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl 2Z A13 433.88 436.09 731 CN1CCN(CC1)c2ccc(Nc3nc(nc(n3)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)cc2 2Z A43 501.96 503.11 732 ClC(Cl)(Cl)c1nc(Nc2ccc(cc2)n3cccn3)nc(n1)C(Cl)(Cl)Cl 2Z A42 469.89 471.09 733 CN1CCN(CC1)c2ccc(Nc3nc(NCCN4CCCC4)nc(n3)C(Cl)(Cl)Cl)cc2 7B A1 498.16 499.10 734 CC(C)(C)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)C1)N3CCOCC3 2E A20 414.08 415.57 735 CC(C)(C)c1ccc(cc1)c2nc(NCc3cccc(CN4CCCC4)c3)nc(n2)C(Cl)(Cl)Cl 2E A52 517.16 518.18 736 CN(CCc1ccccn1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(C)(C)C 2E A19 463.11 464.23 737 CC(C)(C)c1ccc(cc1)c2nc(NCC(C)(C)CN3CCCCCC3)nc(n2)C(Cl)(Cl)Cl 2E A48 511.20 512.22 738 CC(C)(C)c1ccc(cc1)c2nc(nc(n2)C(Cl)(Cl)Cl)N3CCCN(CCO)CC3 2E A23 471.14 472.18 739 CC(C)(C)c1ccc(cc1)c2nc(Nc3ccncc3)nc(n2)C(Cl)(Cl)Cl 2E A15 421.06 422.23 740 NC1CCCCC1NC1═NC(═NC(═N1)C1═CC(Cl)═C(Cl)C═Cl)C(Cl)(Cl)Cl 2C A60 452.98 456.27 741 CC1(C)CC(CC(C)(C)N1)NC1═NC(NC2═CC═CC═C2)═NC(═N1)C(Cl)(Cl)Cl 1G A31 442.12 443.41 742 CN1CCC(CC1)NC1═NC(NC2═CC3═C(C═CC═C3)C═C2)═NC(═N1)C(Cl)(Cl)Cl 1H A12 450.09 451.76

TABLE 12 MS, found Cmpd SMILES Prep. MS, calc'd (M + 1) 743 NC1CCN(CC1)c2nc(nc(n2)C(Cl)(Cl)Cl)c3ccc(cc3)C(Cl)(Cl)Cl 2H 486.95 488.34 744 ClC(Cl)(Cl)C1═NC(NC2═CC═NC═C2)═NC(═N1)C1═CC═C(C═C1)N1CCCC1 2AA 434.06 435.20

TABLE 13 Cmpd IUPAC Name D6 W2 C235 hERG 2 (2-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 162 103 119 3 N,N-dimethyl-1-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]pyrrolidin-3- 198 93 139 100 amine 4 N-[2-(morpholin-4-yl)ethyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 328 173 385 85 5 N-[2-(pyrrolidin-1-yl)ethyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 58 54 62 99 6 4-(3-methoxyphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 33 26 44 96 7 4-(4-methoxyphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 105 80 103 100 8 N,N-dimethyl-1-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]piperidin-3- 307 97 313 75 amine 9 1-[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-N,N-dimethylpyrrolidin-3-amine 36 41 261 59 10 1-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-N,N-dimethylpyrrolidin-3-amine 11 ethyl 4-(4-{[2-(pyrrolidin-1-yl)ethyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 588 475 592 12 ethyl 4-(4-{[3-(pyrrolidin-1-yl)propyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 1000 1000 1000 13 ethyl 4-{4-[3-(dimethylamino)pyrrolidin-1-yl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}benzoate 1000 1000 1000 14 ethyl 4-{4-[(2-amino-2-methylpropyl)amino]-6-(trichloromethyl)-1,3,5-triazin-2-yl}benzoate 37 24 36 11 15 ethyl 4-(4-{[2-(diethylamino)ethyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 52 39 48 84 16 ethyl 4-[4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]benzoate 1000 1000 1000 46 17 ethyl 4-[4-(piperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]benzoate 1000 833.3 1000 35.9 18 4-(4-chlorophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 43 37 46 102 19 4-(3,4-dichlorophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 92 20 1-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-N,N-dimethylpyrrolidin-3-amine 50 21 N-(2-amino-2-methylpropyl)-4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 37 22 2-(3,4-dichlorophenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 33 23 4-(3,4-dichlorophenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 77 25 2-(3,4-dichlorophenyl)-4-(piperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 10 26 4-(3,4-dichlorophenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 246 173 479 10 27 4-(4-methoxyphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 41 37 50 94 28 2-(4-methoxyphenyl)-4-(piperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 586 268 523 32 29 2-(4-chlorophenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 307 173 351 5 30 2-[(2-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)sulfanyl]ethan-1-ol 744 205 573 42.7 31 2-(4-chlorophenyl)-4-(morpholin-4-yl)-6-(trichloromethyl)-1,3,5-triazine 12 32 2-(4-tert-butylphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 167 408 33 33 (2-{[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 151 138 142 41 34 4-(4-tert-butylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 152 141 152 80.9 35 4-[4-(benzyloxy)phenyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 194 125 186 56 36 4-[4-(benzyloxy)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 563 679 37 4-[4-(benzyloxy)phenyl]-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 266 205 314 38 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 163 50 122 81.4 amine 39 4-(4-methanesulfonylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 85 45 92 90 40 2-{4-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 359 175 405 41 2-{4-[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 33 102 290 7.7 42 2-{4-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 1000 416 1000 43 2-(3-methoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 1000 1000 44 4-[4-(methylsulfanyl)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 462 204 638 45 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin- 43 91 74 38 2-amine 46 4-(4-tert-butylphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 47 56 69 25 47 4-[4-(methylsulfanyl)phenyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 95 48 2-(4-methylpiperazin-1-yl)-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazine 449 231 778 49 diethyl[2-({4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 118 134 379 50 4-(4-methylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 51 4-(4-methylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 725 1000 52 4-(4-methylphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 32 22 36 83 53 diethyl(2-{[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 394 228 396 54 2-(4-methanesulfonylphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 432 356 632 55 N-(2-amino-2-methylpropyl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 46 30 89 17 56 N,N-dimethyl-1-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]pyrrolidin-3- 1000 1000 1000 amine 57 N-[2-(pyrrolidin-1-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 10 6 22 25 58 2-(4-methanesulfonylphenyl)-4-(morpholin-4-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 665 1000 59 diethyl[2-({4-[(4-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 290 153 288 100 60 4-[(4-methoxyphenyl)methyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 525 232 491 61 N-(1-methylpiperidin-4-yl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 570 376 556 62 1-methyl-4-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]-1,4-diazepane 9 5 9 31 63 2-N-(2-methoxyphenyl)-4-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine- 603 794 540 2,4-diamine 64 2-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-N-[2-(morpholin-4-yl)phenyl]-6-(trichloromethyl)-1,3,5- 140 75 121 100 triazine-2,4-diamine 65 N-(2-methoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 32 32 31 83 66 2-N-(2-methoxyphenyl)-4-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 549 542 380 67 2-N-(2-methoxyphenyl)-4-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 1000 1000 1000 diamine 68 4-[(2-methoxyphenyl)methyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 69 2-[(2-methoxyphenyl)methyl]-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 1000 1000 70 diethyl[2-({4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 6 6 6 100 71 4-[(2-methoxyphenyl)methyl]-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin- 6 6 6 117 2-amine 72 2-(4-methanesulfinylphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 33 33 27 41 73 2-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-N-[4-(1H-pyrazol-1-yl)phenyl]-6-(trichloromethyl)-1,3,5- 1000 1000 1000 triazine-2,4-diamine 74 diethyl(2-{[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 1000 1000 1000 75 4-(4-methanesulfonylphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin- 635 1000 1000 2-amine 76 1-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 1000 1000 1000 77 4-(4-methanesulfonylphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 92 53 131 72 78 N-(1-ethylpiperidin-3-yl)-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 70 50 90 103 79 4-(4-tert-butylphenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 26 25 36 51 80 N-(1-ethylpiperidin-3-yl)-4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 135 90 129 97 81 1-{4-[(4-ethoxyphenyl)methyl]piperazin-1-yl}-3-[4-(3-{4-[(4-ethoxyphenyl)methyl]piperazin-1-yl}- 633 601 992 2-hydroxypropoxy)phenoxy]propan-2-ol 82 4-[(3-methoxyphenyl)methyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 805 1000 83 4-[(3-methoxyphenyl)methyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 103 68 133 117 84 4-[(3-methoxyphenyl)methyl]-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin- 1000 1000 1000 2-amine 85 N-(1-ethylpiperidin-3-yl)-4-[(3-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 86 N-(1-ethylpiperidin-3-yl)-4-[(4-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 623 600 991 87 N-(1-ethylpiperidin-3-yl)-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 43 32 57 88 N-(1-ethylpiperidin-3-yl)-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 79 69 77 89 4-[(4-methoxyphenyl)methyl]-N-[2-(2-methylpyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin- 805 718 991 50 2-amine 90 4-[(4-methoxyphenyl)methyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 91 4-(4-chlorophenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 31 19 32 79 92 N-{3-[(4-{[2-(1-methylpyrrolidin-2-yl)ethyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2- 122 106 164 yl)amino]phenyl}acetamide 93 4-(4-methanesulfonylphenyl)-N-(pyridin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 995 1000 94 N-(1-ethylpiperidin-3-yl)-4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 396 173 456 95 4-(4-methanesulfonylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 163 86 178 96 1-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 70 51 96 65 97 N-(2-amino-2-methylpropyl)-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 26 20 33 35 98 2-[(2-{[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 448 366 554 yl]amino}ethyl)amino]ethan-1-ol 99 2-(4-methylpiperazin-1-yl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazine 59 12 21 16 100 1-[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 112 69 88 38 101 1-[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 182 117 158 102 1-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 58 44 48 47 103 1-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 24 20 16 34 104 4-(2-methoxyphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 115 53 82 105 4-(2-methoxyphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 145 73 93 106 4-(2-methoxyphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 162 79 106 107 diethyl(2-{[4-(2-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 212 95 158 108 1-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]-1,4-diazepane 70 47 82 28 109 1-methyl-4-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]-1,4-diazepane 100 52 114 110 1-[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 243 142 303 111 1-[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 191 103 232 112 1-methyl-4-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 168 107 209 113 1-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 33 23 35 64 114 4-(2-methoxyphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 70 41 72 95 115 1-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 357 242 360 116 4-(4-tert-butylphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 59 61 73 22 117 N-(2-amino-2-methylpropyl)-4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 55 44 70 14 118 2-(4-(4′-(methylsulfonyl)-5-(trichloromethyl)-[1,1′-biphenyl]-3-yl)piperazin-1-yl)ethan-1-ol 618 399 784 119 2-{4-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 29 12 46 18 120 1-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 123 82 112 15 121 4-(2-methylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 70 42 84 103 122 4-(2-methylphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 172 80 219 123 diethyl(2-{[4-(2-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 57 31 67 124 1-[4-(2-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 108 73 142 125 1-methyl-4-[4-(2-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 180 68 224 126 4-(2-methylphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 22 7 22 127 2-{4-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan- 5 3 9 25 1-ol 128 4-(2-methylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 181 80 204 129 4-(4-methanesulfonylphenyl)-N-methyl-N-{[2-(pyridin-3-yl)phenyl]methyl}-6-(trichloromethyl)- 170 102 233 1,3,5-triazin-2-amine 130 4-(4-methoxyphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 12 5 24 20 131 4-(tert-butyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 302 443 1000 132 2-{4-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1- 64 103 200 ol 133 4-[(2-methoxyphenyl)methyl]-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 784 1000 134 4-(4-methylphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 521 453 1000 135 4-(2-methoxyphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 765 461 1000 136 4-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 378 212 852 137 4-(4-tert-butylphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 246 228 287 138 N-(pyridin-4-ylmethyl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 241 118 407 139 4-(4-chlorophenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 202 81 320 140 4-(4-chlorophenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 106 32 136 11 141 4-(4-chlorophenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 556 237 652 142 4-(4-chlorophenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 306 112 469 143 4-(4-chlorophenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 424 150 513 144 4-[(2-methoxyphenyl)methyl]-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 472 252 563 145 4-(4-methylphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 168 94 344 146 4-(2-methoxyphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 539 246 804 147 4-(4-methoxyphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 155 77 233 148 4-(4-tert-butylphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 621 151 671 149 N-[2-(pyridin-4-yl)ethyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 326 108 380 150 4-[4-(methylsulfanyl)phenyl]-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 380 109 394 151 4-(3-methoxyphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 346 133 549 152 4-[(2-methoxyphenyl)methyl]-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 615.8 1000 153 4-(4-methylphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 199 87 249 154 4-(2-methoxyphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 477 1000 155 4-(3-methoxyphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 318 145 614 156 4-(4-methoxyphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 560 1000 157 4-(3,4-dichlorophenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 298 80 343 158 4-(4-tert-butylphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 260 92 324 159 N-(pyridin-3-ylmethyl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 603 191 635 160 4-[4-(methylsulfanyl)phenyl]-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 789 238 896 161 2-(4-tert-butylphenyl)-4-(piperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 88 32 98 15 162 N-[2-(pyridin-3-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 69 30 90 14 163 N-[2-(pyridin-2-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 50 20 61 5 164 N-(pyridin-3-ylmethyl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 99 33 145 165 N-(pyridin-2-ylmethyl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 82 29 90 20 166 N-[2-(pyridin-4-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 43 13 40 12 167 4-(4-methylphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 423 1000 168 4-(4-methoxyphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 755 338 898 169 4-(3,4-dichlorophenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 640 211 626 170 4-(4-tert-butylphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 313 1000 171 N-(pyridin-2-ylmethyl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 390 183 547 172 4-(4-methylphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 209 106 346 173 4-(3-methoxyphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 302 127 552 174 4-(4-methoxyphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 430 181 641 175 4-(4-tert-butylphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 110 54 165 176 4-(3,4-dichlorophenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 204 80 293 177 4-(4-methanesulfonylphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 355 186 565 178 4-(4-methanesulfonylphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 392 162 518 179 4-(4-methanesulfonylphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 471 201 680 180 4-(4-methanesulfonylphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 819 478 1000 181 4-(2-methoxyphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 471 1000 182 4-(2-methoxyphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 659 256 1000 183 4-(2-methoxyphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1055 344 1000 184 4-(3-methoxyphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 263 114 434 185 4-(4-methoxyphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 185 63 244 186 N-[2-(pyridin-2-yl)ethyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 494 115 499 187 4-[4-(methylsulfanyl)phenyl]-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 317 73 478 188 4-phenyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 176 42 197 189 4-(4-methylphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 213 147 263 190 4-(3,4-dichlorophenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 347 264 551 191 4-(4-tert-butylphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 238 159 287 192 4-(3-methoxyphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 18 13 12 100 193 4-(3-methoxyphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 29 22 17 93 194 tert-butyl N-{1-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]piperidin-4- 138 79 132 yl}carbamate 195 N-(2-amino-2-methylpropyl)-4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 6 6 3 3 196 4-(4-phenylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 31 25 30 53 197 4-(4-phenylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 128 105 137 198 1-[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 64 40 70 199 1-methyl-4-[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 200 N-(1-methylpiperidin-4-yl)-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 201 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 845 1000 202 4-(3,5-dichlorophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 7 10 7 51 203 4-(3,5-dichlorophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 50 59 43 83 204 1-[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 231 78 214 205 1-[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 23 7 26 20 206 4-(3,5-dichlorophenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 207 2-(3,5-dichlorophenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 208 4-(3,5-dichlorophenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 137 62 150 209 4-(3,5-dichlorophenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 122 67 112 210 4-(3,5-dichlorophenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 112 72 78 211 4-(3,5-dichlorophenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 314 148 303 212 N-(1-methylpiperidin-4-yl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 45 16 25 80 213 2-(4-methylpiperazin-1-yl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazine 314 94 186 214 N-(2-amino-2-methylpropyl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 19 11 10 42 215 N-(1-ethylpiperidin-3-yl)-4-(2-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 426 132 248 216 2-(2-methoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 709 244 547 217 N-(2-amino-2-methylpropyl)-4-(2-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 43 20 20 62 218 1-[4-(2-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 104 38 73 219 2-(4-methylpiperazin-1-yl)-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazine 75 19 49 220 diethyl(2-{[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 40 8 12 66 221 2-(4-methylphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 222 4-(3,4-dichlorophenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 22 2 8 68 223 4-(naphthalen-2-yl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 371 43 233 224 4-(naphthalen-2-yl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 33 9 12 41 225 4-(naphthalen-2-yl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 226 1-methyl-4-[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 227 1-[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 29 10 12 18 228 4-(naphthalen-2-yl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 26 6 7 77 229 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 31 6 11 55 230 4-(naphthalen-2-yl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 246 59 212 231 4-(naphthalen-2-yl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 127 57 83 232 4-(naphthalen-2-yl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 238 132 239 233 4-(naphthalen-2-yl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 323 149 196 234 N-(1-methylpiperidin-4-yl)-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 24 15 14 29 235 4-(naphthalen-2-yl)-N-(pyridin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 14 8 10 236 4-(3-methoxyphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 52 50 60 237 N-(1-methylpiperidin-4-yl)-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 47 32 31 107 238 N-(2-amino-2-methylpropyl)-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 570 464 399 239 2-(4-methylpiperazin-1-yl)-4-phenyl-6-(trichloromethyl)-1,3,5-triazine 192 125 158 240 diethyl(2-{[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 221 163 149 241 N-(1-ethylpiperidin-3-yl)-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 963 242 diethyl(2-{[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 64 47 36 243 diethyl[2-({4-[(3-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 199 123 128 244 N-(2-amino-2-methylpropyl)-4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 245 4-(4-methylphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 441 304 289 246 4-(4-tert-butylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 48 59 35 247 4-(4-tert-butylphenyl)-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 139 131 94 248 4-(4-phenylphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 674 920 249 4-(4-phenylphenyl)-N-(pyridin-3-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 545 755 250 4-(4-phenylphenyl)-N-(pyridin-2-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 721 858 251 4-(4-phenylphenyl)-N-[2-(pyridin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 252 4-(4-phenylphenyl)-N-[2-(pyridin-3-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 253 4-(4-phenylphenyl)-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 254 diethyl[2-({4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 632 492 462 255 4-[2-(4-methylphenyl)phenyl]-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 217 159 146 256 N-(1-ethylpiperidin-3-yl)-4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 306 194 220 257 4-(3,4-dichlorophenyl)-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 54 45 29 258 N-[(1-ethylpiperidin-4-yl)methyl]-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 50 29 26 259 N-[(1-ethylpiperidin-4-yl)methyl]-4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 162 105 113 amine 260 N-(2-amino-2-methylpropyl)-4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 85 71 56 62 261 1-methyl-4-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 1000 1000 1000 262 1-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 1000 1000 1000 263 1-{4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 1000 960 763 264 4-[2-(4-methylphenyl)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2- 71 57 57 37 amine 265 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 803 714 672 266 4-[2-(4-methylphenyl)phenyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 654 474 530 267 N-(1-ethylpiperidin-3-yl)-4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 268 diethyl(2-{[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 309 259 282 269 1-(4-(3-methoxybenzyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl)-4-methyl-1,4-diazepane 835 286 627 270 N-(1-methylpiperidin-4-yl)-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 46 43 43 271 N-(1-amino-2-methylpropan-2-yl)-4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 19 10 32 272 2-(4-methoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 1000 1000 273 N-[(1-ethylpiperidin-4-yl)methyl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 319 304 282 amine 274 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 19 19 17 88 275 4-(4-methoxyphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 618 699 276 2-{4-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 1000 1000 1000 277 N-(1-amino-2-methylpropan-2-yl)-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 406 364 312 amine 278 4-(4-methoxynaphthalen-1-yl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 35 17 48 279 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 66 20 77 amine 280 N-(1-ethylpiperidin-3-yl)-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 138 76 193 281 1-[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 148 66 205 282 1-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 154 67 247 283 4-(4-chlorophenyl)-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 97 34 146 284 N-(2-amino-2-methylpropyl)-4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 12 3 18 285 4-(4-chlorophenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 799 567 993 286 (2-{[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 5 2 10 287 1-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 143 60 232 288 2-[(3-methoxyphenyl)methyl]-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 859 197 509 289 1-{4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-4-methyl-1,4-diazepane 810 311 1000 290 1-{4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 138 87 206 291 4-[(2-methoxyphenyl)methyl]-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 231 66 328 292 N-(2-amino-2-methylpropyl)-4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 77 34 103 293 N-[(1-ethylpiperidin-4-yl)methyl]-4-[(2-methoxyphenyl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2- 48 13 70 amine 294 4-[(2-methoxyphenyl)methyl]-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 82 41 167 295 2-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5- 10 10 23 triazine-2,4-diamine 296 2-N-(2-amino-2-methylpropyl)-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine- 302 318 460 2,4-diamine 297 N-(1-ethylpiperidin-3-yl)-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 16 13 28 38 298 2-(4-methylpiperazin-1-yl)-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazine 62 33 87 10 299 4-[2-(4-methylphenyl)phenyl]-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 195 148 311 300 4-(4-methoxynaphthalen-1-yl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 97 82 359 301 2-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5- 1000 1000 1000 triazine-2,4-diamine 302 2-{4-[4-(trichloromethyl)-6-{[4-(trifluoromethoxy)phenyl]amino}-1,3,5-triazin-2-yl]piperazin-1- 166 107 299 yl}ethan-1-ol 303 2-N-[(4-aminooxan-4-yl)methyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5- 43 61 65 triazine-2,4-diamine 304 2-{4-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 80 41 201 305 2-{4-[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 35 23 68 306 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 54 30 87 38 307 N-[(1-ethylpiperidin-4-yl)methyl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 21 10 34 308 2-{4-[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 52 24 126 309 2-(4-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}piperazin-1-yl)ethan-1-ol 188 122 438 310 N-(1-ethylpiperidin-3-yl)-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 13 9 24 311 N-[(4-aminooxan-4-yl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 81 47 169 amine 312 N-(2-amino-2-methylpropyl)-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 8 3 18 65 313 N-[(4-aminooxan-4-yl)methyl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 7 2 14 314 N-[(4-aminooxan-4-yl)methyl]-4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 7 2 16 5 315 N-[(4-aminooxan-4-yl)methyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2- 3 1 8 36 amine 316 N-[(4-aminooxan-4-yl)methyl]-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 11 12 23 38 amine 317 N-[(4-aminooxan-4-yl)methyl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 2 8 20 318 N-[(4-aminooxan-4-yl)methyl]-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 7 2 17 23 amine 319 N-[(4-aminooxan-4-yl)methyl]-4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 16 10 34 320 4-phenyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 11 2 20 321 4-(4-tert-butylphenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 6 3 11 11 322 N-(2,2,6,6-tetramethylpiperidin-4-yl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin- 63 57 103 30 2-amine 323 4-[4-(methylsulfanyl)phenyl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin- 20 17 51 2-amine 324 4-(4-methanesulfonylphenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin- 208 166 391 2-amine 325 N-(2,2,6,6-tetramethylpiperidin-4-yl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin- 123 82 269 2-amine 326 4-(naphthalen-2-yl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 327 4-(4-phenylphenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 33 33 63 20 328 4-(3,4-dimethoxyphenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 64 40 84 31 amine 329 N-(2-amino-2-methylpropyl)-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 561 357 652 330 4-(4-chlorophenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 331 N-(2-amino-2-methylpropyl)-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 36 23 41 332 N-[(4-aminooxan-4-yl)methyl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 46 36 45 333 N-[(4-aminooxan-4-yl)methyl]-4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 26 15 40 334 4-(3-chlorophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 9 2 15 335 4-(3-chlorophenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 15 14 32 99 336 1-[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 74 38 83 337 4-(3-chlorophenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 338 4-(3-chlorophenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 97 56 111 339 4-(3-chlorophenyl)-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 34 14 41 340 N-[(4-aminooxan-4-yl)methyl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 11 8 17 amine 341 2-N-(6-methoxypyridin-3-yl)-4-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5- 7 5 10 triazine-2,4-diamine 342 2-N-[2-(diethylamino)ethyl]-4-N-(6-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 335 149 398 diamine 343 4-(1,4-diazepan-1-yl)-N-(6-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 3 7 344 2-N-(1-ethylpiperidin-3-yl)-4-N-(6-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 80 34 98 diamine 345 N-(6-methoxypyridin-3-yl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 267 199 1100 346 2-N-(2-methoxypyridin-3-yl)-4-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5- 62 52 116 triazine-2,4-diamine 347 2-N-[2-(diethylamino)ethyl]-4-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 975 896 1000 diamine 348 2-N-(2-methoxypyridin-3-yl)-4-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5- 11 9 18 96 triazine-2,4-diamine 349 2-N-(6-methoxypyridin-3-yl)-4-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 124 129 296 diamine 350 2-N-(2-methoxypyridin-3-yl)-4-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 560 467 900 diamine 351 2-N-(2-methoxypyridin-3-yl)-4-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 188 131 327 diamine 352 2-N-[(1-ethylpiperidin-4-yl)methyl]-4-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine- 790.8 637.2 1000 2,4-diamine 353 N-(2-methoxypyridin-3-yl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 101 80 211 354 2-N-(2-methoxypyridin-3-yl)-4-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 682 611 1000 diamine 355 2-N-(1-ethylpiperidin-3-yl)-4-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 38 31 76 diamine 356 N-(2-amino-2-ethylbutyl)-4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 3 7 44 357 N-(2-amino-2-ethylbutyl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 2 2 5 34 358 N-(2-amino-2-ethylbutyl)-4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 301 296 554 359 N-(2-amino-2-ethylbutyl)-4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 45 51 95 360 N-(2-amino-2-ethylbutyl)-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 4 4 9 361 N-(2-amino-2-ethylbutyl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 1000 1000 1000 362 N-(2-amino-2-ethylbutyl)-4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 4 10 10 28 363 N-(2-amino-2-ethylbutyl)-4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 11 14 17 52 364 N-(2-amino-2-ethylbutyl)-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 4 6 25 365 N-(2-amino-2-ethylbutyl)-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 5 5 10 69 366 N-[2-(pyrrolidin-1-yl)ethyl]-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 605 632 775 367 2-N-(6-methoxypyridin-3-yl)-4-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 69 82 175 diamine 368 4-[4-(pyrrolidin-1-yl)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 404 392 624 369 2-N-(6-methoxypyridin-3-yl)-4-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 64 82 134 diamine 370 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin- 846 1000 1000 2-amine 371 1-methyl-4-{4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 1000 1000 1000 372 N-(1-methylpiperidin-4-yl)-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 373 N-(2-amino-2-methylpropyl)-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 409 837 1000 374 2-N-[2-(diethylamino)ethyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine-2,4- 2 5 5 109 diamine 375 4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazin-2-amine 75 107 184 376 N-(2-amino-2-ethylbutyl)-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 8 11 89 377 N-(2-amino-2-ethylbutyl)-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 2 6 8 25 378 4-(1,4-diazepan-1-yl)-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 50 59 98 379 N-(2-methoxypyridin-3-yl)-4-(4-methyl-1,4-diazepan-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 66 92 159 380 4-(4-fluorophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 19 21 36 108 381 4-(4-fluorophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 5 9 14 106 382 4-(4-fluorophenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 17 20 36 105 383 diethyl(2-{[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 15 20 33 102 384 1-[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 25 29 59 385 4-(4-fluorophenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 28 39 57 386 N-[(1-ethylpiperidin-4-yl)methyl]-4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 9 12 20 97 387 N-(1-ethylpiperidin-3-yl)-4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 4 7 13 108 388 N-(2-amino-2-ethylbutyl)-4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 132 98 153 389 N-(2-amino-2-methylpropyl)-4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 30 13 45 390 2-(4-fluorophenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 495 143 567 391 4-(4-fluorophenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 43 19 46 392 4-(3,4-dimethoxyphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 173 69 166 393 4-(3,4-dimethoxyphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 81 37 100 394 4-(3,4-dimethoxyphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 676 360 642 amine 395 (2-{[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 1 2 2 396 N-(2-amino-2-methylpropyl)-4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 86 49 117 397 1-[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 1000 1000 1000 398 1-[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 1000 638 1000 399 4-(3,4-dimethoxyphenyl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 705 1000 400 2-(3,4-dimethoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 564 276 688 401 4-(3,4-dimethoxyphenyl)-N-[(1-ethylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 733 400 726 402 4-(3,4-dimethoxyphenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 428 269 572 403 2-N-(2-amino-2-methylpropyl)-4-N-(6-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 134 78 203 diamine 404 2-N-(2-amino-2-methylpropyl)-4-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 1000 1000 1000 diamine 405 4-phenyl-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 27 16 45 406 4-phenyl-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 77 35 89 407 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 85 39 94 408 1-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 190 84 189 409 1-methyl-4-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 118 43 119 410 N-[(1-ethylpiperidin-4-yl)methyl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 103 35 113 411 diethyl(2-{[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 232 158 312 412 diethyl[2-({4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)ethyl]amine 1000 686 1000 413 1-[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 363 171 365 414 2-(4-methoxynaphthalen-1-yl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 388 120 473 415 N-(2-amino-2-methylpropyl)-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 278 133 261 416 2-{4-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 1000 381 1000 417 2-{4-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 1000 786 1000 418 2-{4-[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 327 128 365 419 2-(4-{4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}piperazin-1-yl)ethan-1-ol 1000 496 1000 420 2-{4-[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 599 210 676 421 2-{4-[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 1000 553 1000 422 2-{4-[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 291 73 310 423 2-{4-[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 765 263 793 424 4-(4-methoxynaphthalen-1-yl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2- 180 91 235 amine 425 4-(4-methoxynaphthalen-1-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin- 289 170 346 2-amine 426 4-(4-methoxynaphthalen-1-yl)-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 239 141 270 427 2-(4-methylpiperazin-1-yl)-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazine 676 459 877 428 1-{4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepane 1000 1000 1000 429 N-(1-ethylpiperidin-3-yl)-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 791 607 912 430 N-[(1-ethylpiperidin-4-yl)methyl]-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 1000 1000 1000 amine 431 2-(4-{4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}piperazin-1-yl)ethan-1-ol 1000 1000 1000 432 N-[(4-aminooxan-4-yl)methyl]-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 1000 1000 1000 amine 433 4-(3-chlorophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 76 44 145 434 (2-{[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 539 367 636 435 1-[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 1000 1000 1000 436 2-(3-chlorophenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 155 19 158 437 N-(2-amino-2-methylpropyl)-4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 27 16 35 438 4-(3-chlorophenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 24 13 46 439 dimethyl(3-{[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)amine 196 82 200 440 (3-{[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 1000 1000 1000 441 dimethyl[3-({4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 1000 1000 1000 yl}amino)propyl]amine 442 (3-{[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 2 1 2 yl]amino}propyl)dimethylamine 443 dimethyl(3-{[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)amine 145 43 161 444 dimethyl(3-{[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)amine 463 183 403 445 dimethyl(3-{[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)amine 151 116 189 446 dimethyl[3-({4-[2-(4-methylphenyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 482 223 535 yl}amino)propyl]amine 447 (3-{[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 591 296 673 448 (3-{[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 35 7 40 449 (3-{[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 194 97 263 yl]amino}propyl)dimethylamine 450 (3-{[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 239 91 252 451 2-{4-[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 154 63 179 452 4-(2-nitrophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 192 41 103 453 2-{4-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 173 43 112 454 2-{4-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 252 64 118 455 2-{4-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 214 65 118 456 2-{4-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan- 207 91 136 1-ol 457 2-(4-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepan-1-yl)ethan-1- 328 80 168 ol 458 2-{4-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 172 44 116 459 2-{4-[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 163 108 153 460 2-{4-[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 594 158 367 461 2-{4-[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 151 27 80 462 2-{4-[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 221 43 104 463 2-{4-[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan- 355 201 306 1-ol 464 2-{4-[4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 177 55 144 465 2-(4-{4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-1,4-diazepan-1-yl)ethan-1- 1000 222 498 ol 466 N-(1-ethylpiperidin-3-yl)-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 279 85 179 467 N-(2-amino-2-methylpropyl)-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 402 123 256 468 2-{4-[4-(trichloromethyl)-6-{[4-(trifluoromethoxy)phenyl]amino}-1,3,5-triazin-2-yl]-1,4-diazepan-1- 34 16 21 yl}ethan-1-ol 469 4-(4-chlorophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 913 176 469 470 4-(3,4-dichlorophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 70 258 471 4-(3,5-dichlorophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 174 1000 472 4-(3-chlorophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 449 51 244 473 4-(4-chlorophenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 474 4-(3,5-dichlorophenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 65 208 527 475 4-(3-chlorophenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 469 86 266 476 4-(3,5-dimethoxyphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 57 23 35 477 4-(3,5-dimethoxyphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 77 23 41 478 4-(3,5-dimethoxyphenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 42 14 22 amine 479 (2-{[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 38 12 17 480 1-[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-4-methyl-1,4-diazepane 307 96 165 481 N-(2-amino-2-methylpropyl)-4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 35 12 17 482 2-(3,5-dimethoxyphenyl)-4-(4-methylpiperazin-1-yl)-6-(trichloromethyl)-1,3,5-triazine 918 222 485 483 2-{4-[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 1000 200 1000 484 4-(4-methylphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 65 30 44 amine 485 4-(3-methoxyphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 94 24 45 amine 486 4-(3,4-dichlorophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin- 25 13 16 2-amine 487 4-(4-chlorophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 64 19 33 amine 488 4-(4-tert-butylphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 27 16 20 amine 489 N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5- 14 8 10 triazin-2-amine 490 4-[4-(methylsulfanyl)phenyl]-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5- 91 49 67 triazin-2-amine 491 4-(4-methanesulfonylphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5- 48 18 34 triazin-2-amine 492 N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5- 95 33 52 triazin-2-amine 493 4-phenyl-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2-amine 33 10 17 494 4-(naphthalen-2-yl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 38 18 23 amine 495 4-(3,5-dichlorophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin- 36 10 13 2-amine 496 4-(4-phenylphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 29 15 14 amine 497 4-(2-nitrophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 913 176 469 amine 498 4-(4-methoxynaphthalen-1-yl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5- 247 66 125 triazin-2-amine 499 4-(3-chlorophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 51 13 20 amine 500 4-(4-fluorophenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5-triazin-2- 285 113 174 amine 501 4-(3,4-dimethoxyphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5- 362 94 241 triazin-2-amine 502 4-(3,5-dimethoxyphenyl)-N-{[1-(propan-2-yl)piperidin-4-yl]methyl}-6-(trichloromethyl)-1,3,5- 127 28 52 triazin-2-amine 503 4-(4-methylphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 44 14 26 504 4-(3-methoxyphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 70 16 32 505 4-(3,4-dichlorophenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 29 17 20 506 4-(4-chlorophenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 31 10 16 507 4-(4-tert-butylphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 43 39 43 508 N-[(1-methylpiperidin-4-yl)methyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2- 34 13 22 amine 509 N-[(1-methylpiperidin-4-yl)methyl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 294 98 167 amine 510 4-(4-methanesulfonylphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2- 416 88 273 amine 511 N-[(1-methylpiperidin-4-yl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin- 77 34 56 2-amine 512 N-[(1-methylpiperidin-4-yl)methyl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 103 30 57 513 N-[(1-methylpiperidin-4-yl)methyl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 118 67 78 514 4-(3,5-dichlorophenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 79 26 28 515 N-[(1-methylpiperidin-4-yl)methyl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 345 235 378 516 N-[(1-methylpiperidin-4-yl)methyl]-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 292 83 181 517 4-(4-methoxynaphthalen-1-yl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin- 23 7 12 2-amine 518 4-(3-chlorophenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 32 11 18 519 4-(4-fluorophenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 14 7 9 520 4-(3,4-dimethoxyphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2- 82 19 45 amine 521 4-(3,5-dimethoxyphenyl)-N-[(1-methylpiperidin-4-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2- 45 14 23 amine 522 4-(2-nitrophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 312 90 216 523 diethyl(2-{[4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 294 79 182 524 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 108 28 70 525 1-[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 43 33 41 526 2-{4-[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-ol 250 74 220 527 4-(3,5-dimethoxyphenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 26 21 24 amine 528 4-(3,5-dimethoxyphenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 35 23 33 529 N-[(4-aminooxan-4-yl)methyl]-4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 59 55 55 530 N-[(1-aminocyclopentyl)methyl]-4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 13 14 13 531 (3-{[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 41 22 35 532 dimethyl(3-{[4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)amine 454 206 355 533 (3-{[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 129 46 90 534 N-methyl-N-[2-(pyridin-2-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 35 12 38 amine 535 4-(4-methylphenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 465 173 439 536 4-(3-methoxyphenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 362 1000 537 4-(4-methoxyphenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 297.8 1000 538 4-(4-tert-butylphenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 545 236.2 557 539 N-[2-(pyrazin-2-yl)ethyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 325 98 270 540 4-phenyl-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 151 88 213 541 4-(naphthalen-2-yl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 236 761 542 4-(4-phenylphenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 651 140 594 543 4-[4-(methylsulfanyl)phenyl]-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 669 1000 544 4-(2-nitrophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 530 1000 545 4-(2,2-dimethyl-2H-chromen-6-yl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 338 147 300 amine 546 4-(4-methoxynaphthalen-1-yl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 361 701 547 4-(4-fluorophenyl)-N-[2-(pyrazin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 332 90 331 548 1-methyl-4-[4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepane 69 53 70 549 2-(4-methylpiperazin-1-yl)-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazine 503 236 663 550 N-(1-methylpiperidin-4-yl)-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 48.05 20.59 35.85 551 N-[(1-ethylpiperidin-4-yl)methyl]-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 70.27 35.6 56.53 552 2-{4-[4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 170.4 76.05 175.6 553 4-(2,2-dimethyl-2H-chromen-6-yl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 18.63 15.06 15.96 amine 554 4-(3,4-dichlorophenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2- amine 555 2-N-(2-amino-2-methylpropyl)-6-(trichloromethyl)-4-N-[3-(trifluoromethyl)phenyl]-1,3,5-triazine- 75.55 30.79 59.58 2,4-diamine 556 2-N-(2-amino-2-methylpropyl)-4-N-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazine-2,4- 24.57 15.15 19.66 diamine 557 2-N-(2-amino-2-methylpropyl)-4-N-phenyl-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 558 4-(4-chlorophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 5 4 6 107 559 4-(4-chlorophenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 17 9 17 100 560 (3-{[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 20 9 18 561 4-(4-chlorophenyl)-N-[5-(pyrrolidin-1-yl)pentyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 39.67 27.84 38.69 63 562 dimethyl(3-{[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2- yl]amino}propyl)amine 563 dimethyl(3-{[4-(trichloromethyl)-6-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2- 5 2 6 82 yl]amino}propyl)amine 564 N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 24.4 16.25 22.65 102 565 dimethyl(3-{[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 39 23 35 31 yl]amino}propyl)amine 566 dimethyl(3-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2- 408.4 248.5 381.5 yl]amino}propyl)amine 567 diethyl(2-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}ethyl)amine 182 60 165 568 diethyl(2-{[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}ethyl)amine 6 4 7 569 N-(1-ethylpiperidin-3-yl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 11 5 12 25 570 N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 571 N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 160.4 88.28 150.4 572 diethyl(2-{[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]amino}ethyl)amine 16 12 16 111 573 [3-({4-[3,5-bis(trifluoromethyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 10 11 11 33 yl}amino)propyl]dimethylamine 574 N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 2 4 5 40 575 4-[3,5-bis(trifluoromethyl)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2- 21.2 16.86 24.22 28 amine 576 [2-({4-[3,5-bis(trifluoromethyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 7 7 8 27 yl}amino)ethyl]diethylamine 577 4-(3,4-dichlorophenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 578 N-(1-ethylpiperidin-3-yl)-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 62.24 36.51 59.15 23 579 N-(1-ethylpiperidin-3-yl)-4-(trichloromethyl)-6-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 36.94 35.35 39.71 41 580 4-[3,5-bis(trifluoromethyl)phenyl]-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 9 4 9 31 amine 581 (2-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 582 diethyl(2-{[4-(trichloromethyl)-6-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]amino}ethyl)amine 26.1 11.75 24.91 54 583 4-(3,4-dichlorophenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 83.6 30.41 69.67 92 584 [3-({4-[3,5-bis(trichloromethyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 781 558 877 yl}amino)propyl]dimethylamine 585 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin- 3 10 6 42 2-amine 586 dimethyl(1-{[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}propan-2- 10 6 14 yl)amine 587 diethyl(3-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}propyl)amine 1000 1000 1000 588 4-[3,5-bis(trichloromethyl)phenyl]-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2- 16 11 17 20 amine 589 N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin- 1000 286.1 1000 2-amine 590 dimethyl(2-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2- 205.6 66.11 172.4 yl]amino}propyl)amine 591 N-[(1-ethylpyrrolidin-3-yl)methyl]-4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2- 249 123 190 amine 592 N-[(1-methylpiperidin-2-yl)methyl]-4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin- 37.53 18.45 27.4 23 2-amine 593 dimethyl(1-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}propan-2- 77 23 41 41 yl)amine 594 ethyl 4-(4-{[(1-ethylpyrrolidin-3-yl)methyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 61 40 85 595 ethyl 4-(4-{[(1-methylpiperidin-2-yl)methyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 101 72 85 596 N-[(1-ethylpyrrolidin-3-yl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- amine 597 1-N,1-N-dimethyl-4-N-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 1000 882 1000 yl]cyclohexane-1,4-diamine 598 ethyl 4-(4-{[3-(dimethylamino)propyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoate 62 31 72 599 (2-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine; 1,4- 1000 1000 1000 bis(trichloromethyl)benzene 600 1,4-bis(trichloromethyl)benzene; diethyl(2-{[4-(trichloromethyl)-6-[4-(trifluoromethyl)phenyl]-1,3,5- 1000 1000 1000 triazin-2-yl]amino}ethyl)amine 601 1,4-bis(trichloromethyl)benzene; diethyl(2-{[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5- 1000 1000 1000 triazin-2-yl]amino}ethyl)amine 602 1,4-bis(trichloromethyl)benzene; N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[3- 1000 853 1000 (trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 603 diethyl(3-{[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]amino}butyl)amine 1000 1000 1000 604 (3-{[bis(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine; 1,4- 224 363 628 bis(trichloromethyl)benzene 605 4-(3,4-dichlorophenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 7 5 5 22 amine 606 (3-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 40 16 24 20 607 1,4-bis(trichloromethyl)benzene; N-[3-(pyrrolidin-1-yl)propyl]-4-(trichloromethyl)-6-[4- 1000 1000 1000 (trifluoromethyl)phenyl]-1,3,5-triazin-2-amine 608 4-(3,4-dichlorophenyl)-N-[(1-methylpiperidin-2-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 62.54 20.1 51.73 44 609 4-(3,5-dichlorophenyl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 264.9 301.9 amine 610 (2-{[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 9 7 11 54 611 (3-{[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 8 4 5 48 612 (2-{[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)diethylamine 19.5 12 18 613 4-(3,4-dichlorophenyl)-N-[1-(1-ethylpiperidin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 25 8 17 88 614 4-(3,5-dichlorophenyl)-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 248 161.7 275.4 615 diethyl(2-{[4-(4-methanesulfinylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}ethyl)amine 1000 1000 1000 616 4-(4-methanesulfinylphenyl)-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 617 1-N,1-N-diethyl-3-N-[4-(trichloromethyl)-6-[3-(trichloromethyl)phenyl]-1,3,5-triazin-2- 211 124 158 yl]cyclohexane-1,3-diamine 618 (3-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propyl)dimethylamine 63.08 53.09 68.23 77 619 2-N-(3,5-dichlorophenyl)-4-N-[1-(dipropylamino)propan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 136 71 132 diamine 620 1-[4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 431 175 409 621 1-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 290 101 319 622 1-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 74 36 59 623 1-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 58 21 32 624 1-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 91 43 62 625 1-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]piperidin-4-amine 47 12 20 626 1-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}piperidin-4-amine 18 7 11 627 1-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 85 25 48 628 1-[4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 42 17 20 629 1-[4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 21 15 19 630 1-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 12 10 13 631 1-[4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 291 153 219 632 1-[4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 64 40 58 633 1-[4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 10 8 10 634 1-[4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 145 62 88 635 1-[4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 259 135 218 636 2-N-(4-chlorophenyl)-4-N-[3-(dimethylamino)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 16 18 40 637 2-N-(3,4-dichlorophenyl)-4-N-[3-(dimethylamino)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 17 13 20 103 diamine 638 2-N-(3,5-dichlorophenyl)-4-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 5 5 5 49 639 2-N-(3,5-dichlorophenyl)-4-N-[1-(dimethylamino)propan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 13 7 9 25 diamine 640 2-N-(3,4-dichlorophenyl)-4-N-[1-(dimethylamino)propan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 8 8 10 23 diamine 641 2-N-(3,4-dichlorophenyl)-4-N-[2-(dimethylamino)propyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 15 5 13 117 diamine 642 2-N-(3,4-dichlorophenyl)-4-N-[1-(diethylamino)propan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 5 3 13 76 diamine 643 2-N-(3,4-dichlorophenyl)-4-N-[1-(1-ethylpiperidin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 47 33 48 100 diamine 644 2-N-(3,5-dichlorophenyl)-4-N-[1-(diethylamino)propan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 131 9 14 100 diamine 645 2-N-(3,5-dichlorophenyl)-4-N-[1-(1-ethylpiperidin-4-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 79.11 37.5 58.86 75 diamine 646 2-N-(3,4-dichlorophenyl)-4-N-[5-(diethylamino)pentan-2-yl]-6-(trichloromethyl)-1,3,5-triazine-2,4- 672.7 735.4 1000 diamine 647 2-{[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]amino}ethan-1-ol 35 23 39 100 648 4-(4-methanesulfonylphenyl)-N-[4-(4-methylpiperazin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin- 30 18 33 13 2-amine 649 N-[3-(azepan-1-yl)-2,2-dimethylpropyl]-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5- 338 196 609 72 triazin-2-amine 650 4-(4-methanesulfonylphenyl)-N-(pyridin-4-ylmethyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 803 1000 651 4-(4-methanesulfonylphenyl)-N-(2-methoxypyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 760 577 1000 652 N-(pyridin-4-ylmethyl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 385 301 876 653 N-methyl-N-{[2-(pyridin-3-yl)phenyl]methyl}-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]- 1000 272.1 1000 1,3,5-triazin-2-amine 654 4-(4-methanesulfonylphenyl)-N-(pyridin-3-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 198 185 271 655 2-N-(1-ethylpiperidin-3-yl)-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine-2,4- 19 11 28 diamine 656 2-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine- 3 2 7 2,4-diamine 657 2-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine- 535 390 731 2,4-diamine 658 4-(4-methyl-1,4-diazepan-1-yl)-6-(trichloromethyl)-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazin-2- 701 625 875 amine 659 4-(1,4-diazepan-1-yl)-6-(trichloromethyl)-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazin-2-amine 19 18 38 58 660 N-[(1-aminocyclohexyl)methyl]-4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 8 9 17 661 N-[(1-aminocyclohexyl)methyl]-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 3 2 8 32 662 N-[(1-aminocyclohexyl)methyl]-4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 663 N-[(1-aminocyclohexyl)methyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2- 729 583 1000 amine 664 N-[(1-aminocyclohexyl)methyl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 18 21 47 amine 665 N-[(1-aminocyclohexyl)methyl]-4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 76 76 147 amine 666 N-[(1-aminocyclohexyl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 3 2 5 amine 667 N-[(1-aminocyclohexyl)methyl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 668 N-[(1-aminocyclohexyl)methyl]-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 1000 1000 1000 amine 669 N-[(1-aminocyclohexyl)methyl]-4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 12 10 23 670 N-[(1-aminocyclohexyl)methyl]-4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 22 20 38 671 N-[(1-aminocyclopentyl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 1000 1000 1000 amine 672 N-[(1-aminocyclopentyl)methyl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 46 30 68 33 673 N-[(1-aminocyclopentyl)methyl]-4-(4-methoxynaphthalen-1-yl)-6-(trichloromethyl)-1,3,5-triazin-2- 1000 1000 1000 amine 674 N-[(1-aminocyclopentyl)methyl]-4-(3,4-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 8 6 18 675 N-[(1-aminocyclopentyl)methyl]-4-(3-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 676 2-N-(1-methylpiperidin-4-yl)-6-(trichloromethyl)-4-N-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine- 1000 1000 1000 2,4-diamine 677 N-[(1-aminocyclopropyl)methyl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 527 910 678 N-[(1-aminocyclopropyl)methyl]-4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 11 12 20 679 N-[(1-aminocyclopropyl)methyl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2- 606 201 1000 amine 680 N-[(1-aminocyclopropyl)methyl]-4-(3-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 100 35 98 681 N-[(1-aminocyclopropyl)methyl]-4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 593 328 750 682 N-[(1-aminocyclopropyl)methyl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2- 68 31 82 amine 683 N-[(1-aminocyclopropyl)methyl]-4-(3,5-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 727 503 795 684 N-[1-(2-methylpropyl)piperidin-4-yl]-4-(2-nitrophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 225 66 155 685 N-[(1-aminocyclohexyl)methyl]-4-(3,5-dimethoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 686 2-N-(naphthalen-2-yl)-4-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 687 tert-butyl 2-{[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl](methyl)amino}acetate 501 501 501 688 1-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]piperidine-4-carboxamide 1000 1000 1000 689 4-(4-methanesulfonylphenyl)-N-[4-(1H-pyrazol-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2- 94 58 171 amine 690 1-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidine-4-carboxamide 1000 670 1000 691 N-(3-{[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}phenyl)acetamide 341 256 705 692 4-(3,4-dichlorophenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2- 32 24 43 amine 693 4-(4-chlorophenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 37 29 69 694 4-(4-tert-butylphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 24 23 37 695 N-[1-(2-methylpropyl)piperidin-4-yl]-4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin- 582 418 675 2-amine 696 4-(4-methoxyphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 697 N-[1-(2-methylpropyl)piperidin-4-yl]-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin- 1000 1000 1000 2-amine 698 N-[1-(2-methylpropyl)piperidin-4-yl]-4-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 699 N-[1-(2-methylpropyl)piperidin-4-yl]-4-(4-phenylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 564 430 746 700 N-[1-(2-methylpropyl)piperidin-4-yl]-4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin- 513 368 567 2-amine 701 4-(3-chlorophenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 282 195 351 702 4-(3,4-dimethoxyphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2- 435 179 480 amine 703 4-(4-methoxynaphthalen-1-yl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5- 324 237 338 triazin-2-amine 704 N-[1-(2-methylpropyl)piperidin-4-yl]-4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-amine 867 223 525 705 tert-butyl 5-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 1000 851.8 1000 diazabicyclo[2.2.1]heptane-2-carboxylate 706 tert-butyl 5-[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 1000 1000 1000 diazabicyclo[2.2.1]heptane-2-carboxylate 707 tert-butyl 5-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]-2,5- 1000 1000 1000 diazabicyclo[2.2.1]heptane-2-carboxylate 708 4-(3,4-dichlorophenyl)-N-[(1,3-dimethyl-1H-pyrazol-5-yl)methyl]-6-(trichloromethyl)-1,3,5-triazin- 319.7 75.2 221 12.2 2-amine 709 N-(3,4-dichlorophenyl)-4-(morpholin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 6.4 710 tert-butyl 5-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-2,5- 145 281 571 diazabicyclo[2.2.1]heptane-2-carboxylate 711 tert-butyl 5-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 812 1000 1000 diazabicyclo[2.2.1]heptane-2-carboxylate 712 tert-butyl 5-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 1000 1000 1000 diazabicyclo[2.2.1]heptane-2-carboxylate 713 tert-butyl 5-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]-2,5- diazabicyclo[2.2.1]heptane-2-carboxylate 714 tert-butyl 5-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane-2- carboxylate 715 tert-butyl 5-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 126 63 185 19 diazabicyclo[2.2.1]heptane-2-carboxylate 716 2-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 540.4 335.2 439.4 717 2-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 259 163 264 718 2-[4-(4-methoxyphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 278.6 77.35 139.2 23.5 719 2-[4-(4-methylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 96 68 114 10 720 2-[4-phenyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 56 35 89 84 721 2-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5-diazabicyclo[2.2.1]heptane 142 69 126 2 722 2-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]-2,5- 9 5 12 14 diazabicyclo[2.2.1]heptane 723 2-{4-[4-(methylsulfanyl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-2,5- 128 92 118 diazabicyclo[2.2.1]heptane 724 2-[4-(4-methanesulfonylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 106 71 110 70 diazabicyclo[2.2.1]heptane 725 4-{2,5-diazabicyclo[2.2.1]heptan-2-yl}-6-(trichloromethyl)-N-[4-(trifluoromethoxy)phenyl]-1,3,5- 64 53 93 triazin-2-amine 726 2-{4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-yl}-2,5- 1000 1000 1000 diazabicyclo[2.2.1]heptane 727 N-(3-{[bis(trichloromethyl)-1,3,5-triazin-2-yl]amino}phenyl)acetamide 256 131 319 728 2-N-[4-(1H-pyrazol-1-yl)phenyl]-4-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazine- 77 27 79 116 2,4-diamine 729 N-[2-(morpholin-4-yl)phenyl]-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 730 N-(2-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 731 N-[4-(4-methylpiperazin-1-yl)phenyl]-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine 229 165 263 732 N-[4-(1H-pyrazol-1-yl)phenyl]-4,6-bis(trichloromethyl)-1,3,5-triazin-2-amine 386 160 584 733 2-N-[4-(4-methylpiperazin-1-yl)phenyl]-4-N[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5- 117 36 87 55 triazine-2,4-diamine 734 2-(4-tert-butylphenyl)-4-(morpholin-4-yl)-6-(trichloromethyl)-1,3,5-triazine 1000 834 1000 735 4-(4-tert-butylphenyl)-N-{[3-(pyrrolidin-1-ylmethyl)phenyl]methyl}-6-(trichloromethyl)-1,3,5- 207.4 60.65 257.5 triazin-2-amine 736 4-(4-tert-butylphenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 445.4 1000 737 N-[3-(azepan-1-yl)-2,2-dimethylpropyl]-4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2- 241.3 101.3 244.2 amine 738 2-{4-[4-(4-tert-butylphenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-1,4-diazepan-1-yl}ethan-1-ol 1000 60.48 239.9 739 4-(4-tert-butylphenyl)-N-(pyridin-4-yl)-6-(trichloromethyl)-1,3,5-triazin-2-amine 23 24 25 26 740 1-N-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]cyclohexane-1,2-diamine 38 11 23 741 2-N-phenyl-4-N-(2,2,6,6-tetramethylpiperidin-4-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 742 2-N-(1-methylpiperidin-4-yl)-4-N-(naphthalen-2-yl)-6-(trichloromethyl)-1,3,5-triazine-2,4-diamine 743 1-[4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-yl]piperidin-4-amine 22 16 14 15 744 N-(pyridin-4-yl)-4-[4-(pyrrolidin-1-yl)phenyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 190 188 290 745 4-[(4-{[2-(pyrrolidin-1-yl)ethyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)amino]phenol 144 80 389 Ex 1 (1-{[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]amino}propan-2-yl)dimethylamine 41.56 29.43 36.75 95 Ex 2 1-[4-(4-fluorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperidin-4-amine 137 78 150 Ex 3 1-{4-[4-(3,4-dichlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazin-1-yl}ethan-1-one 687 198.4 535.2 16.6 Ex 4 4-(4-methanesulfonylphenyl)-N-methyl-N-[2-(pyridin-2-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2- 688 432 1000 47 amine Ex 5 4-(3-methoxyphenyl)-N-[1-(2-methylpropyl)piperidin-4-yl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 190 110 359 Ex 6 tert-butyl 5-[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl]-2,5- 1000 1000 1000 diazabicyclo[2.2.1]heptane-2-carboxylate Ex 7 2-[4-(trichloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,3,5-triazin-2-yl]-2,5- 106 126 192 29 diazabicyclo[2.2.1]heptane Ex 8 2-N-[2-(morpholin-4-yl)phenyl]-4-N-[3-(pyrrolidin-1-yl)propyl]-6-(trichloromethyl)-1,3,5-triazine- 205 113 160 2,4-diamine Ex 9 N-(pyridin-4-yl)-4-(trichloromethyl)-6-[4-(trichloromethyl)phenyl]-1,3,5-triazin-2-amine 7 5 11 5 Ex 10 3-(4-{[3-(dimethylamino)propyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoic acid Ex 11 4-(4-{[(1-ethylpiperidin-4-yl)methyl]amino}-6-(trichloromethyl)-1,3,5-triazin-2-yl)benzoic acid 1000 1000 1000 15 Ex 12 2-{[4-(4-chlorophenyl)-6-(trichloromethyl)-1,3,5-triazin-2-yl](methyl)amino}acetic acid 5 11 4 39 Ex 13 4-({4-[(pyridin-2-ylmethyl)amino]-6-(trichloromethyl)-1,3,5-triazin-2-yl}amino)phenol 1000 1000 1000 Ex 14 4-(3-aminophenyl)-N-[2-(pyrrolidin-1-yl)ethyl]-6-(trichloromethyl)-1,3,5-triazin-2-amine 1000 1000 1000 Ex 15 ethyl 3-(2-nitrophenyl)-2-phenylprop-2-enoate 69 51 73 Ex 16 1-((4-((3,4-dichlorophenyl)amino)-6-(trichloromethyl)-1,3,5-triazin-2-yl)amino)-N,N- dimethylpropan-2-amine oxide

TABLE 14 In vivo Results Cmpd Thompson Assay Rhesus Results 18 (80 × 3) 3/5 Cures 46 (160 × 3) Suppressive  52 (80 × 3) Suppressive 55 (40 × 3) 3/5 Cures; (80 × 3) 5/5 Rhesus: (65 mg/kg once weekly, malaria Cures prophylaxis); (65 mg/kg/day × 7 days, malaria cures) 57 (80 × 3) Suppressive; (160 × 3) 5/5 Cures 62 (80 × 3) 2/5 Cures Rhesus: (65 mg/kg once weekly, malaria prophylaxis); (65 mg/kg/day × 7 days, malaria cures) 72 (80 × 3) Suppressive 79 (80 × 3) Suppressive 96 (80 × 3) Suppressive 97 (80 × 3) Suppressive; (160 × 3) Suppressive  99 (80 × 3) Suppressive 102 (80 × 3) Suppressive 103 (80 × 3) 1/5 Cures (160 × 3) 5/5 Cures 108 (80 × 3) Suppressive 113 (80 × 3) Suppressive; (160 × 3) 4/5 Cures 117 (80 × 3) Suppressive 119 (80 × 3) 4/5 Cures;(40 × 3) 1/5 Cures; 127 (80 × 3) 1/5 Cures 166 (80 × 3) Suppressive 193 (80 × 3) Suppressive 195 (40 × 3) 2/5 Cures; (80 × 3) 5/5 Cures; (160 × 3) 5/5 Cures 214 (80 × 3) 5/5 Cures; (40 × 3) 2/5 Cures 227 (80 × 3) 2/5 Cures 228 (80 × 3) 4/5 Cures; (40 × 3) Suppressive 229 (80 × 3) 3/5 Cures 234 (80 × 3) 4/5 Cures; (40 × 3) Suppressive 235 (80 × 3) Suppressive 274 (80 × 3) Suppressive 312 (80 × 3) 3/3 Cures;(40 × 3) Suppressive 313 (80 × 3) 1/5 Cures 314 (80 × 3) Suppressive 320 (80 × 3) 4/4 Cures; (40 × 3) 1/5 Cures 322 (80 × 3) 4/5 Cures; (40 × 3) 4/5 Cures 328 (80 × 3) 2/5 Cures 365 (80 × 3) Suppressive 376 (80 × 3) Suppressive 380 (80 × 3) 1/5 Cures 559 (160 × 3) 5/5 Cures  565 (80 × 3) 5/5 Cures 569 (80 × 3) Suppressive 585 (160 mpk) 1/5 Cures 613 (80 × 3) 4/5 Cures 638 (80 × 3) Suppressive 641 (80 × 3) 5/5 Cures Rhesus: (65 mg/kg once weekly, malaria (160 × 1) 5/5 Cures; (40 × 3) 2/5 prophylaxis); (65 mg/kg/day × 7 days, malaria cures) Cures 643 (80 × 3) 2/5 Cures 648 (80 × 3) Suppressive 659 (80 × 3) 4/5 Cures 661 (80 × 3) Suppressive 666 (80 × 3) 2/4 Cures 672 (80 × 3) 4/4 Cures 694 (80 × 3) Suppressive 719 (80 × 3) Suppressive; (160 × 3) Suppressive 721 (80 × 3) 2/5 Cures Rhesus: (65 mg/kg once weekly, malaria prophylaxis); (65 mg/kg/day × 7 days, malaria cures) 722 (80 × 3) Suppressive; (160 × 3) 5/5 Cures 724 (80 × 3) Suppressive 728 (80 × 3) Suppressive 743 (80 × 3) 3/5 Cures; (40 × 3) Suppressive Ex. 7 (80 × 3) Suppressive; (160 × 3) 4/5 Cures

To the extent necessary to understand or complete the disclosure of the present invention, all publications, patents, and patent applications mentioned herein are expressly incorporated by reference therein to the same extent as though each were individually so incorporated.

Having thus described exemplary embodiments of the present invention, it should be noted by those skilled in the art that the within disclosures are exemplary only and that various other alternatives, adaptations, and modifications may be made within the scope of the present invention. Accordingly, the present invention is not limited to the specific embodiments as illustrated herein, but is only limited by the following claims. 

1. A compound of formula I

wherein R1 is a 5-10 membered aromatic ring having 0-4 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein each substitutable ring nitrogen is independently substituted by —R, or R1 is benzopyan, branched or unbranched —(C₁-C₆)alkyl, or

wherein Y is —CH, —CR, or N; R2 is a nitrogen attached 5-8 membered monocyclic ring or a nitrogen attached 7-8 membered bicyclo ring system, and further having 0-2 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein and each substitutable ring nitrogen is independently substituted by —R, or R2 is

and wherein: L and L′ are each independently a linker selected from the group consisting of a bond, a substituted or unsubstituted —(C₁-C₆)alkyl- which may be branched or unbranched, and

wherein Ring L is a 5-7 membered cyclic or aromatic ring and m and m′ are independently 0-3; Ra and Ra′ are each independently H or branched or unbranched —(C₁-C₆)alkyl; Rb and Rb′ are each independently —CO₂R, branched or unbranched —(C₁-C₆)alkyl, branched or unbranched —(C₂-C₈)alkyl substituted with an —OR, —NRR′, or —N(O)RR′ group on one of the C2-C8 carbons, naphthyl, or a 3-7 membered ring having 0-2 ring heteroatoms each independently selected from the group consisting of nitrogen, oxygen, and sulfur, wherein each substitutable ring carbon is independently substituted by —Rc, and wherein each substitutable ring nitrogen is independently substituted by —R; Rc and Rc′ are each independently selected from the group consisting of H, halo, trihalomethyl, trihalomethoxy, branched or unbranched —(C₁-C₆)alkyl, phenyl, branched or unbranched —(C₁-C₆)alkyl-OR, —C(═O)R, —CO₂R, —S(O)₂R, —OR, —NO₂, —CN, —NH₂, —NRR′, —NHC(═O)R, —NHC(OR)═O, —C(O)NRR′, —S(O)_(n)R, and —SO₂NRR′ (wherein NRR′ can form a 4 to 6 member ring), wherein n is 0, 1, or 2; and R and R′ are each independently H, branched or unbranched —(C₁-C₆)alkyl, branched or unbranched —(C₁-C₆)alkyl alcohol, or —CO₂—(C₁-C₆)alkyl; wherein where nitrogen is present as a heteroatom, it is at least 2 carbon atoms from any nitrogen atom attached to the triazine ring, and wherein the ring carbons next to a ring nitrogen are not substituted with —OR, —NO₂, —NH₂, —NRR′, —NHC(O)R, —NHC(O)OR, —S(O)_(n)R, or —SO₂NRR; or a pharmaceutically acceptable salt thereof.
 2. The compound according to claim 1, wherein R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2.
 3. A compound according to claim 1, wherein R1 is phenyl, naphthyl, biphenyl, pyridyl, quinolinyl, benzopyran,

where z is 0 or 1,


4. The compound according to claim 1, wherein R1 is

and and Rb is selected from the group consisting of

R2 is

and Rb′ is selected from the group consisting of an amine group,


5. The compound according to claim 1, wherein R1 is phenyl, naphthyl, biphenyl, pyridyl,

and R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2.
 6. The compound according to claim 1, wherein R1 is

and Rb is selected from the group consisting of an amine group,

and R2 is selected from the group consisting of

wherein x is 1-3 and y is 1-2.
 7. The compound according to claim 1, wherein R1 is

and R2 is

and Rb′ is selected from the group consisting of an amine group,

wherein x is 1-3 and y is 1-2.
 8. The compound according to claim 1, wherein R1 is


9. The compound according to claim 1, wherein R1 is


10. The compound according to claim 1, wherein R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is


11. The compound according to claim 1, wherein R1 is phenyl, naphthyl, biphenyl, or

and R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is


12. The compound according to claim 1, wherein R1 is

and R2 is —NRR′, —C(NH₂)RR′, or

where Rb′ is


13. The compound according to claim 1, wherein Rc and Rc′ are each independently selected from the group consisting of t-butyl, Cl, trichloromethyl, F, trifluoromethyl, —CH₃, —NH₂, —NO₂, —(CH₂)NRR′, —NHC(OR)═O, —NHC(═O)R, —NRR′, —OR, —SR, —S(O)R, —S(O)₂R, —COOH, and —COOR.
 14. The compound according to claim 1, wherein R and R′ are each independently selected from the group consisting of H, —CH₃, —C₂H₅, —C₂H₄OH, —CH(CH₃)₂, —CH₂CH(CH₃)₂, and C(═O)OC(CH₃)₃.
 15. The compound according to claim 1, wherein L and L′ are each independently selected from the group consisting of a bond, —CH₂—, —C₂H₄—, —C₃H₆—, —C₄H₈—, —C₅H₁₀—, —CH(CH₃)—, —CH₂CH(CH₃)—, —CH(CH₃)CH₂—, -benzene-, —CH₂-benzene-CH₂—, and -benzene-CH₂—.
 16. The compound according to claim 8, wherein Rc is methyl, t-butyl, halo, trihalomethyl, —S(O)R, —S(O)₂R, —OR, or —COOR.
 17. The compound according to claim 9, wherein the Rc and Rc′ of the R1 group are each independently halo, trihalomethyl or —OR.
 18. The compound according to claim 1, wherein R is H, methyl, ethyl, —CH₂CH(CH₃)₂, and —(CH₂)OH.
 19. The compound according to claim 1, wherein the compound is selected from the group consisting of Ex 1-16 and Compounds 2-745 of Table
 13. 20. The compound according to claim 1, wherein the compound is selected from the group consisting of Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, 322, 641, 638, 643, 613, 6, 18, Ex. 7, 46, 52, 728, 57, 719, 72, 722, 79, 96, 97, 724, 648, 99, 102, 103, 108, 113, 117, 127, 166, 193, 227, 228, 229, 235, 274, 659, 661, 666, 672, 694, 313, 314, 328, 559, 569, 585, 365, 376, 380, and
 555. 21. The compound according to claim 1, wherein the compound is selected from the group consisting of Compounds 55, 62, 721, 119, 743, 195, 214, 234, 312, 320, and
 322. 22. A pharmaceutical composition comprising one or more compounds according to claim 1 and a pharmaceutically acceptable excipient.
 23. A method of treating or inhibiting an infection caused by a Plasmodium spp. in a subject which comprises administering to the subject a therapeutically effective amount of one or more compounds according to claim 1 or a pharmaceutical composition comprising the therapeutically effective amount of the one or more compounds, before, during, and/or after exposure to the Plasmodium spp.
 24. A method of treating a subject suffering from malaria which comprises administering to the subject a therapeutically effective amount of one or more compounds according to claim 1 or a pharmaceutical composition comprising the therapeutically effective amount of the one or more compounds.
 25. A kit comprising one or more doses of one or more compounds according to claim 1 or a pharmaceutical composition comprising the therapeutically effective amount of the one or more compounds packaged together with a supplementary active ingredient, for example, a known antimalarial agent, and instructions for administration and use. 